The LONG TERM GAME of SHORT TERM RENTALS

anneelizabethgannon
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  • INVESTING

Are you ready to take your STR investing to the next level? This podcast is all about digging into the STR game. From learning about market trends, talking to successful investors on their LONG GAME, to educating new investors on the in’s and out’s of STR strategy, our goal is to empower you to build LONG TERM wealth through SHORT TERM RENTAL investing.

Episodes

  1. JAN 15

    Amenities That Perform: How to Invest Without Guessing

    Are Amenities Worth the Investment? It Depends on the Data. In this episode, we tackle one of the most common—and most misunderstood—questions in short-term rental investing: Should you add amenities to improve performance? From hot tubs and saunas to home gyms, pickleball courts, pet-friendly upgrades, and simple workspaces, amenities can absolutely drive higher bookings and longer stays—but only if they are evaluated like a business decision, not a design choice. We break down how high-performing STRs use amenities to replace the hotel or resort experience, and why the best investments aren’t always the most expensive ones. More importantly, we walk through how to evaluate amenities through a true ROI lens—looking beyond nightly rate increases to include maintenance, cleaning, utilities, insurance, wear and tear, and opportunity cost. This episode covers: How to determine whether an amenity actually changes a guest’s booking decision Why revenue alone is only half the equation—and what costs investors often overlook How to track amenities properly using STR-specific accounting (not generic bookkeeping) When smaller, lower-cost upgrades can outperform big-ticket features How tax strategy, depreciation, and energy efficiency factor into ROI Why amenities must be reviewed monthly—not set and forgotten Whether you’re considering a major upgrade or reassessing features you’ve already added, this episode shows how to stop guessing and start measuring—so every dollar invested in your property is intentional, trackable, and profitable. If you want amenities that perform, not just look good, this conversation will change how you evaluate your next move. To learn how we can RE-ACCELERATE your STR performance in 2026 - https://www.re-accelerate.com/

    16 min

  2. JAN 12

    3 Ways to Truly Measure Your STR’s Performance (and Fix What 2025 Missed)

    Podcast Summary: How to Evaluate Your Short-Term Rental’s 2025 Performance In this episode, we break down three practical ways short-term rental owners can evaluate how their property truly performed in 2025—and how to use that data to build a stronger strategy for 2026. Rather than focusing solely on annual totals, the conversation centers on understanding why the numbers look the way they do and where real improvement opportunities exist. 1. Shift from annual totals to weekly performance Instead of judging success by total annual revenue, we explain why STR owners should evaluate performance week by week, especially during peak periods. Weekly analysis reveals whether you hit your target nightly rates, where pricing may have been too low, and how specific events (weather, seasonality, booking gaps) impacted results. This approach provides far more actionable insight than simply knowing what the property earned over the year. 2. Focus on true net revenue—not just gross income The second key area is understanding what portion of your revenue actually belongs to you. Cleaning fees, pet fees, and other pass-through charges often inflate gross revenue but don’t reflect true profitability. We discuss why separating nightly rate revenue from fees is critical for evaluating margins, adjusting pricing, and ensuring expenses like cleaning and supplies are properly covered—especially as costs continue to rise. 3. Re-evaluate your pricing against real competitors Finally, we talk about benchmarking your property correctly. Market averages don’t always tell the full story—especially for properties with unique amenities, premium locations, or standout features. Comparing your STR to truly comparable listings, reviewing booked vs. available dates, and assessing how your listing is presented (including photos) can uncover both underpricing and overpricing issues. The bigger takeaway What worked last year doesn’t have to define next year. With the right data, detailed revenue tracking, and intentional pricing strategy, small changes—like dialing in peak-week rates or better showcasing amenities—can significantly improve performance. Ultimately, strong results start with accurate financial data, thoughtful analysis, and a proactive plan, not just a year-end P&L.   To learn more about how to Re-Accelerate your STR in 2026 - click on the link below : https://www.re-accelerate.com/

    13 min

  3. JAN 3

    Is It a Repair or an Upgrade? The STR Expense Question That Matters

    Podcast Summary Repairs vs. Capital Improvements: Why Getting This Right Still Matters for STR Owners In this episode of The Long-Term Game of Short-Term Rentals, we dive into a topic that often sends owners down a rabbit hole: repairs versus capital improvements—and why the distinction still matters, even in a world where bonus depreciation has changed. At first glance, it can feel like this no longer matters. Many owners assume, “I’m going to write it off anyway, so what’s the difference?” In this episode, we explain why that thinking can cause real problems—not just for taxes, but for financial reporting, budgeting, and even future financing. The Core Difference We start by grounding the conversation in the fundamental rule: Repairs fix something that’s broken or worn out and restore it to working condition Capital improvements add value, upgrade the property, or extend its useful life This distinction affects: How expenses appear on your P&L How lenders view your operating costs How future budgets and projections are built Misclassifying improvements as repairs can make it look like your property has unusually high ongoing expenses, which can hurt performance analysis and financing conversations. Real-World STR Scenarios To make the concept practical, we walk through common short-term rental examples, including: Replacing a broken bedroom door handle → Repair Replacing all flooring on one level of the home → Capital improvement Upgrading plumbing to handle higher guest volume → Capital improvement Replacing a fan motor in an HVAC unit → Repair Replacing an entire HVAC system with an energy-efficient unit → Capital improvement Installing a hot tub to increase nightly rates → Capital improvement These examples help clarify that dollar amount alone isn’t the deciding factor—it’s the purpose and impact of the work. Why Project-Based Tracking Matters A major theme of the episode is the importance of project-based capital improvements. Rather than tracking dozens of small line items, grouping related costs into a single project (for example, “Plumbing System Upgrade – 2026”) makes: Depreciation schedules easier to understand Future planning more accurate Long-term ownership far less confusing Ten years from now, you’ll remember why you spent the money—not just that you bought “parts from Home Depot.” Repairs as a Planning Signal We also discuss how frequent repairs can be a warning sign. Repeated fixes to the same system often indicate: A larger capital replacement is coming Cash is being thrown at an aging asset Downtime risk is increasing Tracking repairs correctly helps owners proactively plan upgrades during slower booking months instead of reacting during peak season. The Bigger Picture This episode isn’t just about tax coding—it’s about: Telling the right financial story Protecting future lending opportunities Building smarter budgets Treating your STR like a long-term business asset If repairs vs. capital improvements felt murky in the past, that’s okay. This episode encourages owners to clean things up, review depreciation schedules, and set better systems going forward. Takeaway Getting repairs vs. capital improvements right isn’t busywork—it’s foundational. When your P&L clearly shows what you’re fixing versus what you’re improving, your numbers make sense, your planning improves, and your long-term strategy gets stronger. Your homework? Apply this thinking to your own 2025 P&L—and carry it forward into every month of 2026.

    13 min

  4. JAN 1

    1099s for Short-Term Rental Owners: What You Need to Do by January 31

    1099s for Short-Term Rental Owners: What You Need to Do (and Why It Matters) In the first STR podcast of 2026, we kick off the new year by tackling one of the most important—and most confusing—January compliance tasks for short-term rental owners: Form 1099s. With the January 31 deadline approaching fast, this episode breaks down what 1099s are, who needs to receive them, and why issuing them is about more than just compliance—it’s about proving you’re running your rental like a business. We cover: Why January is the right time to get 1099s organized (even if it feels early) What Form 1099 is and when it’s required The $600 rule for non-employee service providers Common STR vendors who may need 1099s (cleaners, maintenance, pool service, repairs) How W-9 forms simplify the entire process—and why every vendor should complete one How to handle gray areas, including corporations, property managers, and large vendors What changes when vendors are paid through Venmo, PayPal, Square, or credit cards How property managers fit into the 1099 equation when they pay vendors on your behalf We also discuss practical systems for tracking payments throughout the year using tools like QuickBooks, Stessa, and even bank statements—and why setting this up now makes future years dramatically easier. Finally, we ease a common fear: mistakes happen. While 1099s must be issued by January 31, corrections can be made through March 31, so perfection isn’t required—just action. Key takeaway: Issuing 1099s is one of the simplest ways to reinforce that your short-term rental is an actively managed business, not a passive investment. Having clear vendor policies, collecting W-9s, and meeting filing deadlines puts you a step ahead—and gives you confidence if the IRS ever asks questions. This episode is your roadmap for getting 1099s done right, setting better systems for 2026, and starting the year on solid ground.

    16 min

  5. 12/26/2025

    Last-Minute Year-End Tax Moves for Short Term Rental Owners

    As 2025 quickly comes to a close, this episode of The Long-Term Game of Short-Term Rentals focuses on one question STR owners ask every December: “Is there anything I can still do—right now—to save money on taxes?” The answer, for many owners, is yes—but it’s simpler than people expect. In this episode, we break down expense acceleration, a practical year-end tax strategy for cash-basis short-term rental owners. Rather than spending money you hadn’t planned to spend, expense acceleration is about timing—paying expenses a few days earlier so they count in the current tax year. We explain: Why cash vs. accrual accounting matters before taking any year-end action How paying January expenses in late December can create real tax savings Why mortgage payments are often the most overlooked (and easiest) opportunity Which fixed expenses are ideal candidates for acceleration (utilities, cleaning, internet, insurance, etc.) How accelerating expenses can feel like a “discount” when you’ve had a profitable year We also address common misconceptions, including: Why taking owner distributions before December 31 does not reduce taxable income Why draining bank accounts at year-end doesn’t work as a tax strategy What doesn’t need to be rushed before year-end—and what can safely wait until January Finally, we offer reassurance to owners feeling year-end pressure: outside of expense timing, most planning—P&Ls, cost segregation studies, and performance reviews—can still be done after the calendar turns. The takeaway: If you’re a profitable, cash-basis STR owner with available cash, the final days of the year are about smart timing—not panic spending. Pay what you were already going to pay, lock in the deduction, and leave the deeper analysis for January. We close by looking ahead to 2026 and wishing all STR investors a strong and profitable new year.   For more information about Re-ACCELERATING your SHORT TERM RENTAL INVESTMENT in 2026 click on the link below - https://www.re-accelerate.com/

    8 min

  6. 12/15/2025

    Rising Costs, Rising Opportunity: Inflation and Short-Term Rentals

    Inflation is everywhere—from the grocery store to the cost of cleaners and supplies—but what does it really mean for short-term rental investors? In this episode, we break down how inflation impacts short-term rentals in both challenging and surprisingly positive ways. While rising costs can squeeze day-to-day expenses, real estate remains a natural hedge against inflation, and short-term rentals offer unique advantages that long-term rentals simply don’t. We walk through why property values tend to rise alongside inflation, how fixed-rate mortgages can actually improve cash flow over time, and why the flexibility of short-term rentals allows owners to adjust pricing quickly as costs change. We also discuss the importance of understanding your true operating costs, tracking market-level pricing shifts, and avoiding the fear of raising nightly rates when the entire market is doing the same. The conversation also dives into pricing psychology, the limits of automated pricing tools, and why playing “consumer” in your own market can help you confidently price your property—especially if your rental has unique features that set it apart. We explore long-term equity growth, why turnkey STRs are often undervalued by traditional home pricing tools, and why investors who are already in the market often have an advantage over new entrants. Finally, we talk about the danger of panic-selling during inflationary periods, the value of thinking in three- to five-year models, and why building a clear first-quarter budget can help investors stay grounded during seasonal slowdowns. If you’re a short-term rental owner feeling the pressure of rising costs—or wondering whether inflation helps or hurts your investment—this episode offers practical perspective, strategic guidance, and a long-term framework to help you stay confident and in control.

    12 min

  7. 12/08/2025

    Why STR Budgets Feel Impossible (and Why That’s Exactly the Point)

    Building your 2026 STR budget doesn’t have to be overwhelming. In this episode, we break down variable expenses, cash flow vs. profitability, and how to plan for slow and peak months with confidence.   Building your 2026 short-term rental budget might feel overwhelming—especially during the busy holiday season—but in this episode, we show you why budgeting is actually one of your most powerful tools as an STR investor. We break down the three most common frustrations investors have with budgeting—uncertain variable expenses, cash flow concerns, and slow-season anxiety—and explain why each of these is actually an advantage when used the right way. You’ll learn why being “wrong” in your budget is often the fastest way to gain clarity, efficiency, and control over your property’s performance. We also dive into: How to handle variable expenses like utilities and cleaning with confidence The difference between cash flow vs. true operating profitability Why paying down your mortgage is still building long-term wealth—even when cash feels tight How to plan for slow months and peak months without panic Why knowing your break-even point changes how you price and market your property How budgeting supports both tax strategy and long-term growth If you’ve been avoiding your budget because it feels stressful, confusing, or intimidating—this episode reframes budgeting as a tool for peace of mind, smarter decisions, and sustainable growth in your STR business. Perfect for new and experienced STR investors who want to head into 2026 with clarity and confidence.

    12 min

  8. 12/05/2025

    The Three Biggest Complaints About STR Budgeting—And Why They’re Actually Your Superpower

    The Three Biggest Complaints About STR Budgeting—And Why They’re Actually Your Superpower In this episode of The Long-Term Game of Short-Term Rentals, Anne and Scott tackle a topic that every STR owner knows they should prioritize but often avoid—building the 2026 budget. With the holidays in full swing and year-end chaos setting in, creating a financial plan can easily fall to the bottom of the to-do list. But as they explain, the end of the year is exactly the right time to build a 12-month roadmap. The hosts break down the three most common objections STR owners give when asked to create a budget—and reveal why each one is actually a major advantage. 1. “I don’t know my variable expenses—this is a waste of time.” Anne and Scott debunk the idea that uncertainty makes budgeting pointless. In reality, budgeting is about setting targets, not predicting perfection. Whether it’s utilities, cleaning fees, or seasonal fluctuations, even a rough estimate helps you identify when something is off. As you collect more data, your budget gets stronger—and your operational decisions get smarter. Budgeting becomes a learning tool, not a guessing game. 2. “My property isn’t cash-flow positive—why bother?” They clarify the difference between being cash-flow negative and being operationally profitable. Many properties are profitable on paper but look unprofitable because owners are paying mortgages, debt service, startup furniture costs, or reimbursing themselves. By separating operations from debt, hosts see real profitability—and real opportunities, like DSCR loans or pulling equity to acquire another property. STRs often take a year or more to ramp up; early months are not the full story. 3. “My market is too seasonal—what’s the point of budgeting?” Seasonality is exactly why budgeting matters. A full-year budget helps owners prepare for slow months, understand break-even points, adjust pricing strategy, and get creative during off-peak periods. With a clear plan, owners can fill slower periods with intentional rentals, protect busy months from pressure, and ultimately stabilize annual revenue. By the end of the episode, Anne and Scott reinforce that budgeting is not about perfection—it’s about direction. A simple plan, paired with monthly check-ins, reduces stress, improves decision-making, and creates a clearer path into 2026. As they remind listeners: uncertainty doesn’t go away on its own, but a budget gives you the confidence to navigate it. Tune in next week for more ways to play the long-term game of short-term rentals.

    12 min

  9. 11/28/2025

    Holiday week strategies: How to Stand Out, Stay Booked, and SET SMART TARGETS for 2026

    In this week’s episode of The Long-Term Game of Short-Term Rentals, we dive into one of the busiest (and most revealing) times of the year for STR owners: the holiday season. With more travelers on the road and more hosts entering the market—often for tax advantages—competition has never been higher. But the properties that win aren’t always the biggest or flashiest… they’re the ones that feel unique. We break down: What’s Happening in the STR Market This Holiday Week Why demand is strong—even as supply grows The real booking patterns we’re seeing right now How last-minute travelers can still fill your December calendar Small Amenities, Big Revenue The game rooms, PlayStations, and small add-ons that create major booking lifts How a few “extra touches” can transform off-season weekends Why the past doesn’t define the future—your revenue can jump with thoughtful upgrades Treat It Like a Business: Budgeting for 2026 How to evaluate Q4 performance and identify rate trends What to look for in your 2025 numbers before finalizing your 2026 budget Why conservative projections and small monthly check-ins keep you on track The 30-minute monthly habit that reduces stress and drives long-term success The Mindset That Wins Running an STR is a business—and businesses grow when owners evolve, adapt, and stay engaged. Even simple monthly targets can remind you that while expenses go out, money is also coming in every single week. That perspective alone can lower stress and give you confidence heading into the new year. As we close out this episode, we’re reminding you: This is a long game. The more you work on your property and your numbers, the stronger your results become. Happy holidays, and we’ll see you on the next episode!

    9 min

  10. 11/24/2025 · VIDEO

    STR Weekly Update for the week ending 11.23 - What happened to Marriott's STR business?

    During this week's episode we talk through what is really going on in the STR market...and this week the news that Marriott was ending its relationship with its STR partner is BIG NEWS.  Our experts talk through what we can learn from this news, and what investors can do to make sure they are profitable each and every week!

    12 min

  11. 07/11/2025

    The Long Term Game of Short Term Rentals - Episode 2 - Asset Protection for STRs

    Asset Protection for STRs: What Every Short-Term Rental Owner Needs to Know In this essential episode of Re-Accelerate, Host Anne Gannon welcomes Jeff Hampton—attorney, STR investor, and co-founder of STR Law Guys (https://jeffhamptonlaw.com) - to break down the urgent need for layered asset protection in the short-term rental market. Drawing from real-world lawsuits and years of legal expertise, Jeff shares cautionary tales and practical steps to bulletproof your property—from LLC structuring and liability waivers to commercial insurance and HOA pitfalls. Whether you own one rental or manage a portfolio of 90, this episode will open your eyes to the legal traps most investors miss—and how to avoid them. Learn why insurance policies may not cover you, why your LLC might not be enough, and how to stay compliant (and profitable) across multiple states.

    29 min

  12. 06/23/2025

    The Long Term Game of Short Term Rentals - Episode 1

    Want to grow long-term wealth through short-term rentals? Start here. In this episode, Anne dives into one of the hottest vacation rental markets in the country—the Poconos. She’s joined by Chris Barrett, President & CEO of the Pocono Mountains Visitors Bureau, to unpack what’s driving demand, where the opportunities are, and what every investor should know and check out the Pocono Television Network Whether you're just starting or scaling your STR portfolio, this podcast delivers the insights you need to invest smarter. https://www.re-accelerate.com/

    24 min
  • 12 Episodes

Ratings & Reviews

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out of 5
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About

Are you ready to take your STR investing to the next level? This podcast is all about digging into the STR game. From learning about market trends, talking to successful investors on their LONG GAME, to educating new investors on the in’s and out’s of STR strategy, our goal is to empower you to build LONG TERM wealth through SHORT TERM RENTAL investing.

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