The LONG TERM GAME of SHORT TERM RENTALS

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...

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 spendin...

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...

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 dow...

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...

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 Happenin...

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 ...

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 startin...