Former podcast guest.

That means more cash flow, faster pay-back, and smarter reinvestment.What Is Cost Segregation & Why STRs BenefitCost segregation is the process of breaking down a property’s purchase price (or renovation cost) and reallocating portions of it into shorter depreciation lives (typically 5, 7, 15 years) instead of being lumped into the standard residential/structure life (27.5 or 39 years).For STRs (especially where average guest stays are short and you materially participate) this becomes even more powerful:It accelerates write-offs and frees up cash sooner.It helps you convert your property into an “active business” rather than passive income in the eyes of the IRS, making more deductions usable against other income.Personally I'm a realtor which makes it easy to gain "material participation" as I am classified as a "real estate professional"There are ways to structure a property that is managed by someone else and still qualify.

Because they will get defensive if they feel you are pressuring them.

They got automatically transitioned, and since the guest service fee is now gone, the total price the guest sees is way lower than it should be.

I was listening to a real estate investing podcast (not BiggerPockets) and they had on a guest who invests in co-living properties.

They all have that strong community feel, and properties there are prime "buy and hold" rentals.The $500K price point is going to be your biggest challenge in those specific areas, especially for a home that fits a family of five.

Make Sure Your Direct Booking Funnel Actually WorksDuring events like this, visibility is everything — especially direct visibility.Here’s what to do immediately:Look through your guest databaseTag anyone with an international email or phone numberCreate a simple, targeted email sequenceMention match dates and travel opportunitiesDrive urgency (“fixtures drop Dec 5 — book now before prices surge”)Not all of them will be fans, but some will know someone travelling.This is where the unexpected bookings come from.4.

The IRS looks at when the property was first ready and available for rent, not when you closed or started renovations.So even though you put in 500+ hours, the time spent rehabbing, furnishing, and getting it guest-ready (April–July) would be considered startup activity, not participation in an active rental operation.

-Focused on long-stay corporate guests to minimize wear and tear.Scaling isn’t about buying more — it’s about systemizing what already works.Anyone else here growing through arbitrage or partnerships?

I work primarily in multifamily and short-term rental investing — and over time, I’ve had many conversations with investors about the unfiltered side of real estate: the deals that didn’t go according to plan.Whether it’s unexpected costs, regulatory curveballs, or guest and tenant issues that test your patience, these stories always seem to reveal the same truth — the best investors aren’t just great at finding opportunities; they’re great at managing chaos.Through my investor interviews and real-world deal analyses, I’ve noticed that every “horror story” tends to leave behind one valuable thing: a framework for better decision-making.