How to Achieve Data-Driven Short-Term Rental Success

Short-term rentals (STRs) continue to offer a compelling investment opportunity for real estate investors—if they’re done right.

In a recent podcast episode, Thomas Castelli, CPA, and Ryan Carriere, CPA, sat down with John Bianchi, the founder of STR Search and a self-proclaimed “Airbnb data nerd,” to discuss how investors can navigate regulations, analyze markets, and use data to uncover profitable short-term rental properties.

Who Is John Bianchi?

John’s background is a testament to the power of focusing on a niche and owning it. He has been immersed in Airbnb data for years, helping identify over 200 profitable short-term rentals and achieving a 100% track record in doing so. Formerly the Head of Data for a major STR investment fund, John now runs STR Search, where he guides investors to find deals in the most lucrative markets. He’s created multiple free courses, including a 40-hour Airbnb data deep-dive, all geared toward helping investors understand the numbers behind STR success.

Why STRs Still Work in 2025

Despite headlines suggesting that “Airbnb is dead” or too competitive, John argues it’s all about picking the right market and property. Areas where large groups prefer to stay in a home instead of a hotel—think popular vacation destinations or locales with ample demand—can still provide robust returns. The key is ensuring that local regulations are supportive and that the demand can keep pace with supply.

1. Regulations: Seek out markets where rules already exist and are not under active threat of banning short-term rentals.
2. Market Demand: Confirm that the local economy either welcomes or depends on STRs. Some communities rely heavily on visitor spending, making them more likely to maintain Airbnb-friendly policies.

The 20% Rule (and What It Really Means)

John introduced a simple yet powerful guideline for evaluating potential cash-flowing properties: the 20% Rule. Importantly, this is not a 20% cash-on-cash return. Instead, it’s the ratio of a property’s annual revenue to its purchase price.

For instance:

• If a home costs $500,000, aim for $100,000 in annual revenue.

This quick calculation, combined with more in-depth research, helps gauge if a market can deliver the returns you want. If you consistently find properties meeting or exceeding that ratio, it’s a good indicator the market has cash-flow potential.

Saturation and Sub-Markets

A major concern for many investors is market saturation—whether too many Airbnbs are chasing too few guests. John explains this isn’t as simple as looking at a city’s total listings. You need to filter by “sub-market” or property type. For example, a six-bedroom luxury home with a pool attracts a very different traveler than a downtown one-bedroom condo. Study each sub-market’s supply and revenue trends year-over-year to see if demand keeps pace with new listings.

Amenities Matter

One of the biggest levers you can pull as an STR investor is amenities. Since guests are effectively “buying” a home for a few days, it’s crucial your property offers more bang for the buck than the competition. Whether it’s a hot tub, game room, pickleball court, or thoughtful design touches, these extras help you stand out in a crowded field and charge premium rates.

Considering Out-of-State Investments

Many investors worry about not living near their property. According to John, distance doesn’t have to be a deal-breaker—especially if a local cleaner, handyman, or property manager can handle day-to-day operations. In fact, being “just two hours away” isn’t necessarily better than being “states away” if you rarely visit the property in person anyway. Focus on strong market fundamentals rather than proximity.

The Final Word: Data Is King

Whether you’re exploring a two-bedroom in Miami or a six-bedroom in the Smoky Mountains, data analysis is your foundation. John’s free courses teach you how to filter AirDNA metrics correctly (e.g., 271+ days of availability, 20+ reviews) to find “real” comps. From there, it’s about matching the right amenities to the right demographic, applying the 20% Rule, and ensuring local regulations are STR-friendly.

For investors looking to save time and gain confidence, John offers a one-on-one service through STRSearch.com, guiding clients from market selection to property acquisition, design, and beyond. By connecting them to an “A-Team” of lenders, designers, and managers—often at discounted rates—he aims to make short-term rentals as painless and profitable as possible.

Short-term rentals can still be a powerful wealth-building tool in 2025—if you do your homework. Follow John Bianchi’s data-driven approach, and you’ll be far better positioned to thrive in any market cycle.

Want personalized advice? Schedule a consultation with our team.

Transcript

Introduction & Warm-Up [00:00.992]

Thomas Castelli, CPA

Thank you for tuning in to this week’s episode of the TaxSmart REI Podcast. Today we’re joined with John Bianchi to discuss his secrets to finding winning short-term rental properties. I know everybody out there wants to use the short-term rental loophole to reduce taxes, but sometimes the biggest challenge is just getting started finding the right property. So we’re gonna be discussing that today. We’ll be diving into all of that in just one minute.

John’s Background & STR Experience [01:01.056]

Thomas Castelli, CPA
All right, awesome. All right, so John, thank you so much for joining us today. Could you give our audience just a brief overview of your background and how you got involved with short-term rentals?

[01:10.316] John Bianchi

Thanks guys for having me. I do appreciate it. A little bit of background about myself. I’ll just kind of give my resume so I can build a little bit of credibility real quick and then I’ll kind of give a quick short story of how I got to this place. As of today, within the past three years, I’ve helped identify over 200-plus properties. So I’ve helped other people buy these properties, and they’re all short-term rentals, and every single last one of them is profitable. So we have a 100% track record right now at finding properties that work in the short-term rental world.

The reason being is because I’m obsessed with data—it’s literally all I do. And it’s not even all data, it’s just Airbnb data. For whatever reason, it gets me super excited. You’re able to just see how much every single last person is making, and then you can study it, and replicate it, and it works. It’s kind of like a cheat code when it comes to Airbnb. I’ve been the head of data for Techvestor (the largest short-term rental investment fund in America), and I have my own business called STR Search.

We help identify properties for people to purchase. I’ve got six free Airbnb data courses that teach you my entire process, one of them is 40 hours long—didn’t build it until after finding 120-plus properties.

The backstory is I started off renting a spare bedroom, learned about Airbnb, realized how cool it was. I had another business I didn’t care for, and once I started reading blogs and saw people building businesses on Airbnb, I did it myself—Chicago, downtown Scottsdale, Michigan. COVID wiped that out, but I still loved the industry, so I turned my data skills into a business. That’s how we got to STR Search. The journey has been about eight years.

Are Short-Term Rentals Still Viable in 2025? [03:28.168]

Thomas Castelli, CPA
Yeah, that’s awesome. A lot of people out there looking to find successful properties, and data is always a great approach. With that track record like yours, I’m sure we’ll have a lot to talk about. To start off, we work with a lot of real estate investors across the spectrum—many high-income earners who use short-term rentals to reduce their taxes but also to earn better cash flow. They were really popular a few years ago. What’s your take on the overall short-term rental market in 2025? Still viable?

[04:10.35]
John Bianchi
100%. And I’m biased, but the industry is still maturing. Regulations help us figure out where STRs work and don’t work. If you can find a property in a market where the regulations allow for it and there’s demand, you can absolutely cash flow. It’s about finding the right price and right demand. I’ve studied 350 markets and found 15 to 20 that work flawlessly.

Evaluating Regulation Risk [06:27.242]

Ryan Carriere, CPA
That’s awesome. Before more questions, let’s touch on regulations. It’s been a big topic in recent years. Is there a simple way to see if regulation risk is low or high?

[07:02.958]
John Bianchi
I’m not good with legalese, so I lean on others, but I look for markets that already have regulations. No regulation at all is risky—if they impose something later, you’re out. Also make sure the local community is okay with it; check articles, Facebook groups, etc. And consider if the economy relies on STRs—if so, they’re probably not going away.

Data Analysis & the 20% Rule [08:40.864]

Thomas Castelli, CPA
Great answer. From a data perspective, what should investors be looking at when selecting a market in 2025?

[08:56.445]
John Bianchi
Check regulation first, then saturation. But even before saturation, ensure the property can cash flow. I use the “20% Rule”: not 20% cash on cash, but 20% price-to-rent ratio. If the house is $500k, I want it to generate $100k revenue. That’s a quick litmus test to see if a market might work. Then you can do a deeper dive.

Saturation & Sub-Market Breakdown [12:24.494]

John Bianchi
People worry too much about saturation, but here’s what it means: are there too many Airbnbs for the demand in that area? In Miami, for instance, I saw 22,000 active listings but also huge traveler demand, so the supply and revenue were moving together. You also have to focus on subcategories—like six-bedroom luxury homes versus one-bed condos. Each has different demand and competition.

Tom’s Condo Scenario in Miami [16:20.992]

Thomas Castelli, CPA
I’m re-listening to all this, because I might underwrite a condo in downtown Miami. Super helpful.

[16:53.228]
John Bianchi
Sure, we can talk about that quickly. Start with building regulations—HOA, city regs. Then on AirDNA, filter to the “good data”: properties with 271+ days available, 20+ reviews in the last 12 months (1-3 reviews/month). That shows true full-time listings. From there, consider views, design, amenities, and be honest about comps. Have a base comp you know you can beat, then move up.

Amenities & Guest Experience [22:31.604]

Ryan Carriere, CPA
Speaking of amenities, you’ve mentioned them a few times. How do you decide which are must-haves?

[22:56.108]
John Bianchi
I tell people to imagine two similar Airbnbs: if yours has more amenities (like a game room, hot tub, pickleball, etc.), your guests get more for the same cost. Who is your demographic? Families, bachelor parties, etc.? Tailor amenities to them. Match what your competition has (must-haves), then add extra “wow” amenities if your budget allows.

Smaller Units & Viability [26:58.016]

Thomas Castelli, CPA
Great explanation. Another question: you said short-term rentals are often for group stays, but do two-bedrooms work?

[27:29.73]
John Bianchi
They can. I just haven’t personally done it. In big cities, though, competition is fierce. For example, Miami has thousands of one-bedroom or two-bedroom listings, plus hotels. Not saying it won’t work—just do the data research carefully.

The Break-Even Mindset & Recession Fears [30:30.392]

John Bianchi
If you’re only aiming to break even, that can be risky if a recession hits. Travel is the first thing people cut. You want a property that can be top 10% in its category, so you still get bookings even if you drop your rates to match others.

Alternative Strategy: Buy Cheaper for Cash Flow [36:02.062]

John Bianchi
Another angle: if you have $700k, maybe get a $400-500k place that cash flows well, then use those profits to afford the $700k condo later. That’s my own strategy.

Out-of-State vs. Local Investing [38:09.066]

John Bianchi
A lot of people want to be within driving distance, but that often means lower returns. With one Airbnb, you’ll mostly rely on a local cleaner or handyman anyway, so it’s practically the same as if you’re in another state.

Short-Term Rental Loophole & Tax Strategy [44:10.154]

Ryan Carriere, CPA
Many of our clients want the short-term rental loophole to offset income. Where do you point them first?

[44:59.318]
John Bianchi
Regulations again, but also the data. The biggest mistakes high-net-worth folks make: they pick a “fun” market that’s dead or overpay for a pretty property. Use AirDNA, do the 20% Rule, find a market with regulation in place, then do a deep dive. All you really need to get right from the start is the data—everything else (like guest experience) can be fixed.

Working with John & STR Search [50:24.042]

Ryan Carriere, CPA
Can’t believe you give away so much for free. If someone wants direct help, how do they work with you?

[50:43.086]
John Bianchi
I only offer one service. All my content is free, but if you don’t have time or want support, hire me and my team at STR Search. We guide you to find a profitable property, introduce you to the “A-Team”—lender, designer, management, cost seg, etc. Because we bring them business, they give discounts that offset our fee. We aim to get you top-tier properties that can withstand recessions.

Conclusion & Final Remarks [52:52.448]

Thomas Castelli, CPA
That’s awesome. So it’s STRSearch.com?

[52:58.014]
Thomas Castelli, CPA
We’ll drop that in the show notes. I’ve checked out some of your YouTube videos and it’s great stuff.

[53:19.19]
John Bianchi
Appreciate it. Also, we launched a free STR Tax Loophole course with Brandon. We have that plus a 7-day Airbnb Data Masterclass on our site.

[53:59.86]
Ryan Carriere, CPA
Amazing.

[54:04.402]
Thomas Castelli, CPA
All right, John, thanks again for coming on and sharing the knowledge. That’s STRSearch.com. Links will be in the show notes.

[54:11.406]
John Bianchi
Thank you.

[54:12.608]
Ryan Carriere, CPA
Thanks!

Disclaimer: This podcast summary and transcript were partly generated and may contain some errors or miss key points from the audio recording.