Episode Summary

Luke and Tyler sit down for a real-time catch-up as Luke races to bring two new short-term rentals online before year-end. One is Alm Haus, Luke’s first major renovation, and the other is a newly acquired “tree house vibe” property near Bellaire.

They unpack winter booking softness, renovation realities, vendor coordination during the holidays, and why soft openings with trusted guests can save you from costly mistakes. The episode also dives into the tax-driven urgencybehind getting properties live, smart amenity decisions in ski markets, and why sometimes “good enough” is better than waiting for perfect.

If you’ve ever tried to launch a property in December… this one will feel very familiar. 😅

🔑 Key Takeaways

• Winter bookings may feel softer than previous years and require more active pricing and listing tweaks
• Major renovations create compounding delays if timelines aren’t tightly managed
• Soft openings with friends, family, or trusted guests help identify issues before full-price bookings
• To capture first-year tax benefits, properties must be operational and meet short-stay requirements
• Bookings that cross into the new year count toward next year, not the current one
• Sleep setup matters: multiple king bedrooms often outperform bunk-heavy layouts
• In ski markets, hot tubs are table stakes, not a luxury
• Differentiation matters: geo domes vs barrel saunas should align with your guest avatar
• Wayfair Professional and Amazon Business can be leveraged for scheduled deliveries and faster setups
• Strong local relationships can solve operational problems faster than throwing money at them
• Launching with solid DIY photos is acceptable short-term if professional photos are scheduled

⏱️ Episode Timeline

• 00:06 Intro and the reality of launching under pressure
• 02:24 Winter booking slowdown and active pricing strategies
• 03:36 Alm Haus renovation update and lessons learned
• 05:30 Holiday staffing challenges and contingency planning
• 06:30 Soft openings and using trusted guests to work out issues
• 07:38 Why year-end timing matters for STR tax strategy
• 10:53 The “Tree House” property and why the prior owner struggled
• 13:28 Bedroom layouts and multi-family demand
• 14:17 Why hot tubs are non-negotiable in ski markets
• 15:17 Amenity decisions based on guest avatar
• 17:36 Wayfair Pro delivery scheduling and rapid setup planning
• 19:25 Outsourcing time-intensive tasks during short property visits
• 22:08 Creative vendor solutions and relationship-driven operations
• 24:31 Photography strategy: launching now, upgrading later
• 26:45 Wrap-up and call to action

💬 Notable Quotes

• “The only show where you get to take pleasure from our pain.”
• “The name doesn’t matter nearly as much as whether I can get the domain.”
• “You have to get up and running at some point.”
• “People up north are just a different breed — and that matters in this business.”

⚠️ Disclaimer

This episode is for informational and entertainment purposes only and does not constitute legal, tax, or financial advice. Always consult with your own attorney, CPA, or financial professional regarding your specific situation.

Summary

In this Real Talk episode of the Peak Season Podcast, Luke opens up about something every short-term rental host eventually hits: end-of-season burnout. Between wrapping renovations, racing toward year-end tax deadlines, juggling slow-season bookings, and navigating holiday stress, it’s a lot.

Luke shares the simple mental framework he leans on when the entrepreneurial pressure cooker gets too hot — a three-part reset he calls State, Story, Strategy. You’ll learn how to quickly get out of your own head, regain clarity, and turn overwhelm into manageable action steps. It’s practical, it’s honest, and it’s something you can use today.

Keywords

short-term rentals, burnout, host stress, holiday season, renovation pressure, STR business, mindset for entrepreneurs, coping strategies, end of year tax planning, overwhelmed hosts, productivity reset, STR tips, property management stress

Takeaways

• Burnout shows up fast when renovations, deadlines, and holiday chaos collide.
• Before tackling your to-dos, reset your state — your physical condition.
• Your story shapes your emotional reality. Reframe overwhelm with gratitude.
• Most stress comes from narratives we repeat, not actual tasks on our list.
• Breaking down stressors into actionable micro-steps creates real momentum.
• Many tasks aren’t solvable today — and that’s okay. Identify the ones that are.
• Temporary stress is often the price of long-term, meaningful growth.
• A clear mind leads to a clear strategy — and far better execution.

Episode Title

The Three S Reset: How Hosts Can Beat End-of-Season Burnout

Disclaimer

This podcast is for informational purposes only and is not financial, legal, or tax advice. Always consult with a professional who understands your specific situation before making decisions related to your business or finances.

Summary

In this solo episode, Luke takes listeners behind the curtain of PriceLabs and breaks down the features most hosts overlook—Market Dashboards and comp sets. Luke shares how he analyzes competitor pricing and occupancy, how he builds comp sets that reveal real market patterns, and why triangulating data leads to smarter, more profitable pricing decisions. If you’ve ever opened PriceLabs, clicked around, and pretended you knew what you were looking at… this episode will get you genuinely dangerous (in the good way).

Takeaways
A deep dive into the parts of PriceLabs most hosts never touch.
How Luke builds comp sets that give meaningful competitive insight.
Tracking competitors’ pricing and occupancy without guessing.
Using Market Dashboards to benchmark your listing like an investor.
Why multiple comp sets > one generic list of neighbors.
Building listing-specific comp sets inside PriceLabs.
Populating KPIs that actually tell you a story.
Triangulating data to avoid bad pricing decisions.
Why subscribing to dashboards keeps you ahead of seasonal swings.
How Luke uses comp sets strategically in his own portfolio.

Chapters
00:00:12 — Why this episode matters
00:00:53 — Market Dashboards explained
00:01:42 — How Luke selects comp sets
00:04:29 — Using Market Dashboards effectively
00:05:19 — Benchmarking your listing
00:06:09 — Managed comp sets: pros and cons
00:07:08 — Building comp sets per listing
00:11:48 — How Luke triangulates data
00:14:17 — Populating KPIs that matter
00:15:30 — Using comp sets for real strategy

Disclaimer
This podcast is for informational purposes only. It is not financial, legal, or tax advice. Always consult with a qualified professional before making decisions related to your business, pricing strategy, or short-term rental operations.

Summary

In this episode of the Peak Season Podcast, Luke walks through seven practical tips for making the most of your visits to your vacation rental property. He covers how to choose the right timing, why solo trips often lead to better efficiency, and how simple organization—like keeping running lists—can make each visit more productive.

Luke also touches on the value of batching errands, hiring help for small but time-consuming tasks, documenting your property with updated photos and videos, paying attention to details guests will notice, and taking a moment to experience the property the way a guest would. Each strategy is designed to streamline your operations, reduce stress, and elevate the overall guest experience.

Takeaways

• Thoughtful timing of your visits helps protect revenue.
• Solo trips allow you to stay focused and efficient.
• Lists keep tasks organized and prevent important items from slipping through the cracks.
• Consolidating errands saves time and simplifies your workload.
• Outsourcing smaller tasks frees you up for more important decisions.
• Regularly documenting the property supports smoother long-term management.
• Attention to small details can directly impact guest satisfaction.
• Experiencing the property as a guest reveals improvements you may otherwise miss.
• Understanding the guest perspective leads to better hosting decisions.
• Consistent maintenance adds long-term value to the property.

Chapters

00:00 — Introduction to Property Visits
02:34 — Timing Your Visits Effectively
05:32 — Traveling Solo for Efficiency
07:54 — Organizing Your Tasks and Lists
10:12 — Maximizing Your Time at the Property

Peak Season Podcast Disclaimer

This podcast is for educational and entertainment purposes only. Nothing in this episode should be considered legal, financial, or tax advice. Please consult the appropriate professional for guidance related to your business.

✨ Summary

In this episode of The Peak Season Podcast, Tyler Kostich opens up about his inspiring journey from military service and a W2 career in human resources to becoming a full-time entrepreneur in real estate and consulting. He shares how short-term rentals became both a passion and a business, the role of family support in his transitions, and the lessons learned about fulfillment, gratitude, and automation. This is a story of courage, connection, and carving out a life aligned with personal values.

⏱️ Chapters

• 00:00 – Introduction to Tyler Kostich
• 05:54 – Transitioning to Real Estate Investing
• 18:11 – Leaving the W2 Job: A Personal Journey
• 22:01 – Future Goals and Aspirations
• 23:47 – Closing Thoughts

📣 Hashtags

#PeakSeasonPodcast #RealEstateInvesting #ShortTermRentals #Entrepreneurship #CareerTransition #PersonalGrowth #Gratitude

🦃 Summary

In this Thanksgiving special of the Peak Season Podcast, Luke and Tyler dig into one of the most underrated levers in the STR world: holiday bonuses for cleaners. They break down how to decide on bonus amounts, why timing matters, and creative ways to show appreciation beyond cash. The duo highlights how gratitude, recognition, and treating your team like actual humans (wild concept, we know) creates better service, happier guests, and a stronger business all year long.

🎯 Takeaways

• A solid baseline bonus for cleaners is the cost of one full clean.
• A little gratitude goes a long way—say it early, say it often.
• Holiday timing makes appreciation feel more meaningful.
• Recognized cleaners tend to deliver better service (shocker).
• Personalized touches strengthen long-term relationships.
• Plan bonuses ahead so you’re not panic-Venmoing on Christmas Eve.
• There are endless creative ways to show appreciation—explore them.
• Generosity and kindness build a culture people want to work in.

🎙️ Episode Title Options

• Holiday Bonuses: A Guide to Gratitude
• The Art of Appreciating Your Cleaners

⏱️ Chapters

00:00 – Thanksgiving greetings & intro to holiday bonuses
02:30 – Who should receive bonuses in your STR business
03:10 – How to divide bonuses among cleaning teams
03:14 – What holiday bonuses look like for cleaners
05:06 – When and how to hand out bonuses

📘 Disclaimer

This podcast is for educational and entertainment purposes only. Nothing here is business, financial, or legal advice. Always consult your own professionals before making decisions.

🎙️ Summary

In this episode of the Peak Season Podcast, we dive into Luke’s real estate journey — from his early days in long-term rentals to discovering the world of short-term rentals and the markets that shaped him. Luke shares the wins, the mistakes, and the mindset shifts that helped him grow not just as an investor, but as a person.

He opens up about the Smoky Mountains, why Northern Michigan captured his heart, and how understanding markets, taking risks, and learning through experience helped define his investment strategy. Whether you're a first-time buyer or building your STR portfolio, Luke’s story offers relatable insights, practical advice, and the real-life lessons that only come from getting in the game.

🔑 Keywords

short-term rentals, real estate investing, market selection, Smoky Mountains, Northern Michigan, investment advice, property management, growth mindset, entrepreneurship, podcast

📘 Takeaways

• Luke transitioned from long-term rentals to short-term rentals in 2022.
• Understanding market dynamics is crucial for successful investments.
• Emotional connections to properties can enhance the investment journey.
• Knowing your numbers is essential before purchasing a property.
• Procrastination delays opportunities—clarity + action wins.
• Unique properties in less competitive markets often yield better returns.
• Networking and mentorship accelerate long-term success.
• Real estate rewards calculated risks and long-term thinking.
• Time often heals real estate “mistakes” if you stay committed.
• Growth happens when you lean into discomfort.

⏱️ Chapters

00:00 — Introduction to the Hosts and Their Journey
01:40 — Luke's Background and Entry into Real Estate
04:05 — Transitioning to Short-Term Rentals
05:40 — Choosing the Right Market for Investment
08:35 — Experiences in the Smoky Mountains
11:26 — Exploring Northern Michigan's Unique Opportunities
13:47 — The Importance of Comfort in Uncertainty
15:11 — New Property Developments in Bel Air
17:56 — Advice for First-Time Short-Term Rental Buyers
22:40 — Expanding Your Short-Term Rental Portfolio

📌 Summary

In this episode of The Peak Season Podcast, Luke and Tyler explore the growing world of co-hosting — a smart alternative to traditional property management for Airbnb and Vrbo owners. They break down what co-hosting is, how it works, and why it’s becoming the go-to solution for property owners who want to maximize revenue, save time, and maintain control without the full workload of self-management.

Luke and Tyler also dive into the practical benefits: how co-hosting can improve guest experiences through strategic outsourcing, proactive maintenance, and hands-on communication, all while helping owners maintain high reviews, consistent branding, and long-term investment growth. By the end of the episode, listeners will understand how partnering with the right co-hosting team can transform their properties, streamline operations, and enhance both profits and lifestyle.

🔍 Keywords

co-hosting, short-term rentals, Airbnb, Vrbo, property management, revenue growth, guest experience, outsourcing, investment property, hosting strategy, STR operations, property maintenance

💡 Takeaways

• ✔️ Co-hosting helps property owners save substantial time and money compared to full-service management.
• ⭐ High reviews are essential to long-term co-hosting success.
• 🧳 Outsourcing cleaning, maintenance, and guest services elevates the guest experience.
• 💰 Co-hosting often delivers better financial outcomes than traditional management.
• 🙋 Ideal clients are owners who don’t have the time or passion to self-manage.
• 📈 Co-hosting can increase property revenue by 25–40%.
• 🏖️ Owners get to enjoy their properties more — without the stress of managing them.
• 🧠 Co-hosts bring strategic marketing, pricing, and operational expertise.
• 🔧 Outsourcing maintenance saves time and reduces headaches.
• ⏳ Co-hosting is an investment in both property performance and personal time.

⏱️ Chapters

00:00 — Introduction to Co-Hosting
04:18 — Financial Benefits & Revenue Potential
11:42 — Operational Efficiencies & Time Savings
18:20 — Who Makes the Ideal Co-Hosting Client
25:05 — Enhancing Guest Experience Through Outsourcing
31:30 — Long-Term Outlook & Co-Hosting as an Investment Strategy

⚠️ Disclaimer

This podcast is for informational and entertainment purposes only. Nothing in this episode should be considered legal, financial, or tax advice. Every investor’s situation is different, and you should always consult with a qualified professional before making decisions related to your short-term rental business.

In this episode of the Peak Season Podcast, Luke and Tyler break down one of the most critical (and underrated) skills in the short-term rental industry: handling difficult guests.

From unexpected complaints to avoidable misunderstandings, they share real-world examples and proven strategies for keeping guest interactions smooth, professional, and empathetic.

Listeners will learn how to deescalate tense moments, communicate clearly, document everything, and implement proactive systems that reduce friction before guests even arrive. Whether you’re an Airbnb host, a property manager, or scaling your rental portfolio, this episode offers actionable insights to improve your guest communication, hospitality standards, and overall STR operations.

Keywords 🔑

short-term rental, Airbnb hosting, guest complaints, STR management, property management, hospitality, guest communication, rental business, guest experience, customer service for hosts, Airbnb problems, handling difficult guests, short-term rental tips, Airbnb hosting strategies

Takeaways 🚀

• Difficult guests are a normal part of the STR business.
• Fast, clear communication solves 90% of issues.
• Empathy + professionalism = your superpower.
• Documentation protects you from false claims.
• Small gestures (like a gift card or quick fix) can change the outcome.
• Knowing local quirks helps you set expectations better.
• Proactive systems prevent the most common problems.
• Clear listing details reduce misunderstandings.
• Every tricky guest makes you a better operator.
• Building rapport early reduces negative reviews.

Chapters ⏱️

00:00:00 — Introduction & Episode Setup
00:03:12 — The Reality of Guest Complaints
00:08:47 — Handling Difficult Situations Calmly
00:14:55 — Communication, Empathy & Professionalism
00:20:38 — Lessons Learned & Actionable Tips
00:24:10 — Final Thoughts & Host Takeaways

Disclaimer

This podcast is for informational and entertainment purposes only. Nothing in this episode should be considered legal, financial, or tax advice. Every investor’s situation is different, and you should always consult with a qualified professional before making decisions related to your short-term rental business.

📌 Summary

In this episode of The Peak Season Podcast, hosts Luke and Tyler get real about one of the most stressful operational challenges in the short-term rental world: losing trusted members of the cleaning team. When two key cleaners suddenly step away, it could feel like a major setback — especially while expanding a property portfolio.

Instead of panicking, the guys break down how they turned this pain point into an opportunity to elevate their cleaning operations, improve quality control, and build a more resilient structure for future growth.

They dive into what it takes to cultivate strong relationships with team members, create transparency in expectations, and ensure trust is at the center of every partnership. From recruiting and onboarding to quality assurance and communication strategies, this conversation offers practical insights for hosts scaling responsibly — without burning out or compromising guest experience.

At its core, this episode is a guide to adapting, improving, and scaling your team in ways that support both today’s needs and tomorrow’s growth.

🔍 Keywords

business growth, team management, short-term rentals, property management, cleaning crew, scalability, transparency, trust, relationships, cleaning operations

💡 Takeaways

• ✔️ Lessons learned: “We make mistakes so you don’t have to.”
• 📉 Shrinking team + 📈 growing business = proactive problem-solving required
• 🤝 Strong relationships are the backbone of operational success
• 🔎 Transparency & clear expectations build trust and loyalty
• 📦 Scalability depends on flexibility — and the people behind the processes
• 🧽 Quality cleaning is non-negotiable in STR success
• 🏘️ Growth must align with what your team can realistically support
• 🌐 Leveraging local talent and resources strengthens long-term operations
• 🎯 Hiring should align with your business values and hospitality standards
• 🔁 Continuous refinement through communication and feedback

⏱️ Chapters

00:00 — Introduction: The Reality of Operational Growing Pains
05:42 — When Key Team Members Move On
12:18 — Rethinking the Cleaning Structure for Scale
20:30 — Trust, Accountability, and Relationship-Driven Management
29:55 — Building a Team That Supports Long-Term Growth

📌 Summary

In this episode of The Peak Season Podcast, hosts Luke and Tyler explore the growing influence of technology in the short-term rental industry. With countless tools promising more bookings and smoother operations, the real challenge is identifying which solutions truly add value — and which create unnecessary complexity.

They break down the core tech categories every host should consider, including dynamic pricing, property management systems, AI-powered communication, and ranking tools. The focus: leveraging technology to elevate the guest experience while maintaining the personal touch that great hosting is built on.

🔍 Keywords

short-term rental, STR tech stack, property management software, dynamic pricing, AI guest communication, direct bookings, RankBreeze

💡 Takeaways

• ✅ The right tech stack can streamline operations and grow revenue.
• ⚠️ Too much tech can complicate your workflow and overwhelm guests.
• 🧩 Property management software serves as the foundation of efficient hosting.
• 📈 Dynamic pricing tools help maximize revenue year-round.
• 🤖 AI communication improves speed and consistency, but personality still matters.
• 👥 Human oversight ensures hospitality and avoids tech failures.
• 📧 Building your own email list drives direct bookings and repeat stays.
• 🚀 Tools like RankBreeze help boost Airbnb listing visibility.
• 💡 Tech should enhance hospitality — not replace it.

⏱️ Chapters

00:00 — Introduction: Why Tech Matters
04:12 — Property Management Software
12:30 — Dynamic Pricing Tools
18:55 — AI in Guest Communication
27:40 — Balancing Tech with Personal Hospitality
35:10 — Direct Bookings and Email Capture

🎧 Episode Summary

In this episode of The Peak Season Podcast, Tyler and Luke break down what guests really want — based on insights from over 500 stays across multiple markets. They dive deep into guest psychology, unpacking why reviews matter more than price, how “value for money” actually works, and what separates a good stay from a great one. From spotless spaces and seamless communication to local experiences and small surprises, this conversation is packed with practical takeaways to help hosts level up hospitality, boost reviews, and stand out in competitive markets.

💡 Takeaways

• Guests trust reviews more than pricing.
• Fast, friendly communication wins every time.
• “Value” is about quality and reliability, not being the cheapest.
• Cleanliness is the baseline, not a bonus.
• Local touches turn good stays into memorable ones.
• Predictability + small surprises = delighted guests.
• Proactive hosts prevent negative reviews before they start.
• Clear check-in instructions are non-negotiable.
• Strong Wi-Fi and transparency build trust.

🔑 Keywords
guest insights, reviews, communication, cleanliness, hospitality, short-term rentals, Airbnb tips, guest psychology, value for money, local experiences

🎧 Summary

In this episode of The Peak Season Podcast, Luke and Tyler dive into what it really takes to survive and thrive in rural short-term rental markets — drawing from their hands-on experience in Northern Michigan. From guest acquisition and seasonality to maintenance challenges and small-town dynamics, they explore the unique factors that shape life as a rural host.

You’ll hear proven strategies for building vendor relationships 🤝, mastering dynamic pricing 💸, and communicating proactively 💬 to create great guest experiences even when resources are limited. Luke and Tyler also highlight the hidden advantages of rural hosting — less competition, stronger community connections, and the chance to offer experiences that guests can’t find anywhere else.

🔑 Keywords

rural markets, short-term rentals, Northern Michigan, guest acquisition, seasonality, connectivity, maintenance, community relations, vendor relationships, dynamic pricing, proactive communication, unique amenities, rural hospitality, small-market strategy

💡 Takeaways

• Build strong local relationships. Reliable vendors and service providers are the foundation of every successful rural STR.
• Use dynamic pricing intentionally. Adjust rates to capture demand surges and fill gaps during slower periods.
• Communicate proactively. Set expectations early to prevent surprises and keep guests happy.
• Lean into your strengths. Showcase amenities like hot tubs, saunas, and fire pits — the details guests remember.
• Market locally and socially. Use social media, tourism boards, and community pages to attract the right audience.
• Plan for limited connectivity. Provide printed directions, offline maps, and clear expectations for Wi-Fi.
• Be a good neighbor. Transparency and respect build long-term community trust.
• Diversify income. Add upsells like early check-ins, firewood bundles, or local experiences.
• Prepare for seasonality. Save reserves during peak months to smooth out shoulder-season dips.
• See rural as opportunity. Less competition means more room for creativity and sustainable growth.

⏱️ Chapters

00:00 – Introduction and Overview
03:00 – Guest Acquisition and Marketing
09:00 – Connectivity and Access Challenges
15:00 – Maintenance and Vendor Relationships
21:00 – Seasonality and Cash-Flow Management
27:00 – Community Relations and Trust
33:00 – Closing Thoughts and Key Takeaways

Description / Summary:
In this episode of The Peak Season Podcast, Luke and Tyler break down the mystery behind the Airbnb algorithm—and how hosts can use it to their advantage. From pricing strategy and calendar management to conversion rates and guest engagement, they reveal the levers that actually move your listing up in search results. You’ll learn why success on Airbnb isn’t random, how to keep your listing “fresh,” and what it really takes to maintain visibility in a competitive market.

Key Takeaways:

• Success on Airbnb is strategic—not luck.
• Airbnb’s algorithm rewards listings that convert well and engage guests.
• Fast response times dramatically improve ranking.
• Overpricing can push your listing out of visibility.
• Regular listing updates signal activity and help you stay relevant.
• Conversion rate is one of the strongest ranking signals.
• Great reviews and consistent Superhost performance boost credibility.
• Keep your calendar open for a full year to capture more searches.
• Engaged hosts create trust—and trust drives bookings.

Keywords:
Airbnb algorithm, visibility, pricing strategies, guest engagement, reviews, Superhost status, vacation rentals, booking success, listing optimization, host strategies

🎙️ Bonus Episode: Navigating the New Airbnb Fee Structure

Keywords: Airbnb, property management software, fees, short-term rental, hosts, pricing strategy, market impact, direct bookings, hospitality industry

💬 Summary

In this bonus episode of The Peak Season Podcast, Tyler and Luke tackle Airbnb’s major update to its host fee structure — a 15.5% service fee that goes into effect on October 27th for hosts using property management software (PMS). This marks a major shift from Airbnb’s split-fee model, where costs were previously shared with guests.

They break down what this change means for short-term rental hosts, how to adjust your pricing strategy to stay profitable, and why now is the perfect time to double down on direct bookings. The conversation cuts through speculation and focuses on clear, actionable steps every host should take before the change goes live.

👉 Learn more about how we help hosts adapt at www.upstreamvacations.com.

🧭 Key Takeaways

• 💰 Hosts using PMS will now pay a 15.5% Airbnb fee on total bookings.
• 🚫 Guests will no longer see service fees — hosts absorb the full cost.
• 🧾 Audit your listings and update pricing before October 27th.
• 🏠 Unique and well-reviewed properties will remain competitive.
• 💌 Build an email list to grow your direct booking traffic.
• 🎁 Offer value-driven discounts to maintain guest loyalty.
• 📈 Engaged, proactive hosts will protect their rankings and profitability.

🎧 Sound Bites

"It's a big impact."
"You need to audit your listing."
"We're engaged hosts."

⏱️ Chapters

00:00 — Bonus Episode Intro
01:53 — What’s Changing in Airbnb’s Fee Structure
03:18 — Who’s Impacted by the Airbnb Fee Increase
04:00 — What Hosts Using a PMS Need To Do Before Oct. 27th
06:55 — Pricing Strategy Adjustments and Direct Booking Opportunities

⚠️ Disclaimer

This bonus episode of The Peak Season Podcast is for informational and educational purposes only. Every property and market is unique—listeners should evaluate what works best for their situation. Luke, Tyler, and Upstream Vacations are not responsible for outcomes resulting from actions taken based on this discussion

🎙️ Episode: Avoid These Costly Hosting Mistakes

Keywords: short-term rental, hosting mistakes, pricing strategy, preventative maintenance, guest experience, Airbnb, direct bookings, vacation rentals, revenue management, property management

💬 Summary

In this episode of The Peak Season Podcast, Luke and Tyler break down the five costly mistakes that can quietly drain profits and momentum from your short-term rental business. From ignoring data-driven pricing to skipping preventative maintenance, they expose the habits that hold hosts back—and share exactly how to fix them.

Discover how small “micro moments” elevate your guest experience, why relying solely on Airbnb limits your growth, and how building your own direct booking channel unlocks true independence. Whether you’re managing one cabin or scaling a portfolio, this episode delivers practical insights to help you run your short-term rental like a business, not a hobby.

👉 Learn more about what we do at www.upstreamvacations.com.

🧭 Key Takeaways

• 💸 Price with data, not gut feelings—and adjust often for local events.
• 🧰 Preventative maintenance prevents expensive surprises.
• 🎁 Small, thoughtful touches create “micro moments” that drive five-star reviews.
• 🌐 Don’t rely solely on Airbnb—diversify your booking channels.
• 🏡 A direct booking website builds repeat guests and trust.
• 📊 Treat hosting like a business, not a side hobby.
• 🗓️ Create seasonal checklists to stay ahead of wear and tear.
• 🤝 Use social media to engage past guests and generate direct bookings.
• 🔍 Every host can improve—success comes from learning and adapting.

🎧 Sound Bites

"Pricing needs to move with the market."
"You need a direct booking website."
"Everything is figureoutable."

⏱️ Chapters

00:00 — Introduction to Costly Mistakes in Hosting
02:59 — Mistake 1: Pricing by Gut, Not Data
05:38 — Mistake 2: Neglecting Preventative Maintenance
07:40 — Mistake 3: Forgetting the Micro Moments
09:59 — Mistake 4: Relying Solely on Airbnb
12:52 — Mistake 5: Treating Hosting Like a Hobby
14:51 — Wrap-Up and Takeaways

⚠️ Disclaimer

The discussions and insights shared on The Peak Season Podcast are for educational purposes only. Every property and market is different—listeners should evaluate strategies in light of their own circumstances. Luke, Tyler, and Upstream Vacations assume no responsibility for outcomes resulting from the use of this content.

🎙️ Episode: Mastering Five-Star Reviews in Airbnb Hosting

Keywords: Airbnb, five-star reviews, guest experience, hospitality, short-term rentals, customer service, property management, guest communication, surprise and delight, feedback

💬 Summary

In this episode of The Peak Season Podcast, Tyler K. and Luke dive deep into what it really takes to earn and maintain five-star reviews as a short-term rental host. They unpack how consistent excellence isn’t luck—it’s the result of systems, communication, and intentional hospitality. From pre-arrival prep and surprise touches to guest education and post-stay follow-ups, this conversation covers how to build trust, elevate experiences, and turn happy guests into loyal advocates.

👉 Learn more about what we do at www.upstreamvacations.com.

🧭 Key Takeaways

• ⭐ Five-star reviews are the result of intentional systems, not chance.
• 💬 Proactive communication sets expectations and prevents misunderstandings.
• 🎁 “Surprise and delight” moments make stays truly memorable.
• 🧾 Educate guests about the review process before checkout.
• 🔁 Follow up after departure to thank guests and gather feedback.
• 🌟 Transparency builds trust and long-term relationships.
• 🙌 Responding to reviews shows professionalism and care.
• 🏡 Creating a warm, thoughtful atmosphere drives repeat stays and referrals.

⏱️ Chapters

00:00 — The Importance of Five-Star Reviews
02:04 — Prepping Guests for Success
05:09 — Surprise and Delight: Creating Memorable Experiences
09:02 — Educating Guests During Their Stay
12:08 — Setting Expectations for Checkout
14:35 — Closing the Loop: Follow-Up After Checkout
20:59 — Wrap-Up and Final Thoughts

⚠️ Disclaimer

The ideas and discussions shared on The Peak Season Podcast are for informational and educational purposes only. Always evaluate what fits your own business model and local regulations. Luke, Tyler, and Upstream Vacations are not responsible for any outcomes resulting from actions taken based on this content.