All Forum Posts by: Melissa Haworth

You're definitely looking in a great direction with Destin and Panama City Beach. The Emerald Coast has become a hotspot for short-term rentals, especially for investors looking to take advantage of bonus depreciation and strong seasonal cash flow. I’ve seen a lot of interest in this area, and for good reason.

Both Destin and PCB pull in steady tourism from spring through early fall. If you can snag a property near the beach or with great views, you're looking at high nightly rates, especially for homes that can host larger groups. It’s a family vacation destination at heart, which means longer stays and solid bookings during peak seasons.

From a tax perspective, Florida is super friendly. There’s no state income tax, and properties in this region work well for cost segregation studies, making that bonus depreciation even more attractive.

Now, there are a few things to keep in mind. Insurance premiums have been rising, so make sure you're running those numbers early on. Some HOAs are very STR-friendly, but others have limits on rentals, like minimum-night stays or permit requirements, so it's important to read the fine print before jumping in.

Also, while the high season can be incredibly profitable, the off-season does slow down a bit. As long as your numbers are conservative and you’re not relying on year-round peak performance, the returns here can still be excellent.

If you're looking at a specific neighborhood or property type, I’m happy to share more detail. The Emerald Coast has a lot of upside if you know how to navigate it.

You're spot on to be thinking critically about saturation and long-term cash flow, especially with the Orlando/Davenport area being such a well-known STR hub. While it's great for personal use (and certainly magical for families), the sheer volume of listings can make it tougher to stand out unless you're offering something truly unique.

If your goal is stronger cash flow and less saturation, I’d suggest expanding your search to Florida’s Panhandle specifically Destin and Panama City Beach. These markets tend to fly a bit more under the radar for out-of-state investors, but they pack a serious punch in peak-season returns. We're talking beachfront appeal, strong tourism draw, and a bit more breathing room when it comes to competition. Plus, many properties here are either fully managed or Airbnb-ready, making them investor-friendly.

You mentioned concerns about insurance and that’s fair. Rates have crept up across Florida, but the Panhandle can sometimes offer more manageable premiums compared to South Florida. Still, it’s wise to get quotes early in your due diligence process to avoid surprises.

As for out-of-state alternatives: parts of the Carolinas are solid bets, especially the mountain or coastal markets in NC (think Asheville or the Outer Banks), but Florida's no state income tax and year-round beach demand still give it a leg up for many investors.

Happy to chat more if you’d like any specific numbers or market insights

Hey—first off, thank you for sharing this. You’re definitely not alone in feeling the pressure of rising insurance costs in the Panhandle, especially after 2023 and 2024 hit a lot of owners harder than expected. What you’re dealing with is frustrating, especially when it stems from something that wasn’t made totally clear during the buying process.

Unfortunately, insurance claims do follow the property in Florida, not the owner—so even if you had nothing to do with the original damage, that previous claim can impact your premiums for up to five years. It’s one of those fine-print items that rarely comes up unless you’re working with an insurance-savvy agent or dig into the CLUE report (which most buyers don’t even know to ask about).

Here are a few things you might consider:

• Keep shopping for insurance annually – Even if the claim sticks around for a while, different carriers weigh these claims differently. Sometimes bundling with another property or personal policy (if you have one) can also help reduce your rate.
• Talk to an STR-focused insurance broker – Not all brokers are created equal. Some specialize in short-term rentals and know which carriers are more forgiving when it comes to past claims. If you need a referral, I’m happy to share a couple I trust in the Panhandle.
• Consider your revenue strategy – You mentioned switching to long-term rental, but that likely won’t help on the insurance front and may put you in the red due to DSCR loan terms. Instead, is there a way to optimize your STR income? Tweaking your pricing strategy, refreshing your listing, or targeting off-season bookings more aggressively might help bridge the gap while insurance settles over time.
• Revisit your expense breakdown – I’ve seen some owners work with financial pros or property managers to restructure things (like utilities, maintenance, or cleaning fees) and claw back a few hundred a month. It’s not glamorous, but every bit helps when insurance is eating so much of the pie.

Paying $700+ a month in insurance hurts, no question. But you’ve got options to soften the blow—and you're clearly staying proactive, which is the best place to be. I’m happy to connect offline or point you toward some vetted vendors if you want to dig deeper.

Hang in there—this market has strong bones, even if the last couple of years have tested all of us.

Hey, welcome to the world of property investing—glad you’re here.

It’s awesome that you’ve got a background in arts and interior design. Honestly, that puts you ahead of the game when it comes to furnishing and staging a short-term rental. A well-designed space makes a huge difference, not just for photos but for guest experience and reviews.

You’re right—Chicago isn’t exactly the easiest market for STRs these days. A lot of investors are looking to other parts of the country with fewer restrictions and stronger vacation demand. Florida, especially the Panhandle (think Destin and Panama City Beach), has been a hot spot for exactly those reasons.

What makes these areas appealing:

• Steady tourist traffic all year
• More affordable than other coastal markets
• Regulations that are generally investor-friendly
• Plenty of local property management options if you’re not planning to self-manage

Since you already know how to create a beautiful space, the next step is learning how to run the numbers and identify areas where STRs actually perform well. I always suggest looking at things like local regulations, seasonal occupancy trends, and what kind of returns people are getting in a specific neighborhood—not just the city overall.

Happy to share more about what’s working in my market if that’s helpful. You’ve got a great foundation already—it’s just about pairing your skills with the right location and strategy.

Hi there,
You're in good company—several of my out-of-state clients have started their STR journeys for the exact same reason: offsetting capital gains through bonus depreciation, cost seg, and material participation. The good news? You're thinking about all the right things, and your timeline is still workable if you act decisively.

I'm a Florida real estate agent and STR investor who works exclusively with out-of-state buyers, and I specialize in helping people exactly in your position find the right markets fast—without cutting corners on due diligence. Here are a few thoughts based on your criteria:

Market Selection:

You need a market that is:

• Historically strong in STR demand
• Zoned appropriately (avoid gray areas)
• Favorable for year-round bookings (since your 500 hours need to be earned in one calendar year)

In my experience, Florida's Panhandle—especially Destin, Panama City Beach, and 30A—checks all of these boxes. These are well-established vacation rental markets with strong occupancy, supportive STR regulations, and a reliable seasonal + off-season guest flow. Properties can also be purchased with cost segregation and depreciation in mind, especially if you focus on newer builds or units with clear component separation.

Analysis Paralysis is Real:

What you're experiencing—research loop, second-guessing—is totally normal for first-time STR investors under pressure. What helps most is picking a proven market, narrowing in on a specific zip code or neighborhood, and working with a team that knows STR performance inside and out. It reduces guesswork and speeds up your decision-making significantly.

Material Participation:

Given your need to hit that 500-hour threshold, I recommend:

• Self-managing or co-hosting (at least for year one)
• Keeping detailed records of hours and tasks performed
• Choosing a market where you can build systems quickly—not from scratch

Florida markets, for example, already have turnkey vendors, automation-ready PMs, and reliable data to help you hit the ground running.

If you'd like, I can walk you through a few specific STR-friendly buildings and neighborhoods where my clients are seeing strong performance and bonus depreciation opportunities. Time is tight, but the right guidance can help you move with clarity instead of panic.

Happy to be a resource as you navigate this next step!

Hi there from a fellow Melissa!
First off, I love your vision—and your approach is spot-on. As a Florida real estate agent and STR investor who works primarily with out-of-state (and international!) buyers, I can tell you that your skill set as a designer + contractor duo gives you a major head start. Add your STR background and real estate experience into the mix, and you're already light years ahead of most first-time investors.

You're also tapping into a niche I’ve seen perform really well lately: luxury 1 bed, 1 bath accommodations. So many couples and solo travelers want high-end touches without the extra bedrooms—and there’s absolutely room in the market for well-designed, upscale small-space stays. It’s a category with growing demand and relatively limited supply, especially in vacation markets that have traditionally focused on larger homes.

A few key pieces of advice I give my international clients starting out:

1. Understand your financing limits and tax implications early. DSCR loans are a great tool for Canadians investing in the U.S., but make sure you're working with a lender experienced in cross-border investing, as well as a CPA who understands U.S. and Canadian tax laws.
2. Know the STR regulations before you fall in love with a property. Some counties (and even HOAs) in Florida, the Carolinas, and Georgia have strict rules on short-term rentals. This one detail can make or break your whole plan.
3. Build a strong local team. Managing remotely is absolutely doable—many of my clients do it successfully—but it hinges on having reliable boots on the ground. A great cleaner, handy person, and property manager (or a really dialed-in tech stack) can make all the difference.
4. Don’t underestimate the power of design. Guests shop with their eyes. Since you already do design work, use that to create a brand and guest experience that feels cohesive and high-end, even in a smaller footprint. This is what gets you premium nightly rates and glowing reviews.

I love your long-term goal of scaling to a boutique hotel—your experience and clarity of vision tell me you're going to get there. If you’re ever considering the Florida Panhandle (Destin, 30A, or Panama City Beach), that’s my niche, and I’d be more than happy to share insights on what’s working well for investors in this market.

Excited for you two—this is such a fun and rewarding journey!

Hi Louie,
Congratulations on taking the leap—what an exciting chapter ahead. With your depth of experience across both the private and public sectors, you're bringing a powerful foundation into this next phase.

As a Florida real estate agent and short-term rental investor, I work with a lot of clients who are pivoting into new ventures—many of them during times of market uncertainty. What I’ve found time and time again is that the people who thrive are the ones who understand that disruption creates opportunity, and clearly, you’re already dialed into that mindset.

Wishing you all the best as you launch your business. If you ever explore opportunities in Florida's STR market, especially along the Panhandle, I'd be glad to connect.

Hi Robert,
Love this conversation—thank you for starting it. As a Florida real estate agent and short-term rental investor who works almost exclusively with out-of-state buyers, I’m seeing more and more clients open to new construction as a strategy, especially in high-demand vacation markets like the Panhandle.

You're absolutely right—most investors are still circling the same outdated listings, throwing offers at properties that need full gut jobs and sell above asking. Meanwhile, some of the savviest clients I work with are quietly building modern, rental-optimized properties for less than market value—and cash-flowing faster because of it.

That said, here’s what tends to hold people back:

• Perceived complexity – Out-of-state investors often don’t know where to begin when it comes to vetting builders or navigating permitting in a different county.
• Timeline fears – Many assume building will take too long to generate income, especially compared to a turnkey.
• STR-specific uncertainty – They’re unsure how to balance design decisions with what actually performs in a short-term rental, especially in coastal, regulated markets.

But once we break it down and pair them with the right team—builder, agent, PM—it’s a completely different story. They get a purpose-built rental with premium finishes, stronger bookings, and fewer maintenance surprises down the line.

So yes, I'm a big believer in building—but only when it's done with a clear understanding of the local STR market and guest expectations. That's where the real ROI lives.

Hi Brett,
Melissa here—I'm a Florida real estate agent and investor who works specifically with out-of-state buyers looking to turn properties into short-term rentals here in the Sunshine State.

You're asking all the right questions. Treasure Island is a resilient market, and in the wake of recent storms, we’re seeing price points that are starting to look like 2021–2022 levels. For investors, that can be a smart window of opportunity—especially this close to the water.

Your winter-use, break-even-the-rest-of-the-year strategy is a common one among my clients from colder states, and it can absolutely work—if the unit is positioned right. In a market full of similar 2 bed, 2 bath condos, the things I have noticed as keys to standing out are:

• Thoughtful design and finishes – Updated interiors and coastal character go a long way.
• Amenities that enhance the guest experience – Think beach gear, a solid workspace, great Wi-Fi, and curated local touches.
• Professional presentation – Listings with strong branding, quality photos, and compelling copy consistently outperform the “copy-paste” crowd.
• Understanding STR regulations – You're correct: policies vary by building and association. Some allow weekly rentals, others require 30-day minimums. Knowing this before you buy is critical.

If you'd like, I'd be happy to share insights on STR-friendly buildings in Treasure Island or connect you with trusted local property managers who work with out-of-state owners.

Best of luck with your search—this could be a great time to dive in.

Available to provide my insight and assistance!