All Forum Posts by: Kyle Wheeler

 Hey Stefanie,

We have a couple of clients who have good multi family properties available in St Petersburg! Reach out anytime, I would love to connect! Thanks, Kyle

Man, I felt this one hard.

I had the same realization not too long ago — thinking I was “building a portfolio,” when in reality I was just collecting properties that looked good on paper but weren’t doing much for me in real life. Once I actually ran the numbers (cash-on-cash, true expenses, opportunity cost), it was like a slap in the face.

I think a lot of us fall into the landlord trap early on — we’re managing properties, dealing with tenants, and calling it investing, but there’s no real strategy behind it. That shift from owning to optimizing is where things start to change.

It’s a tough pill to swallow, but also a powerful one. Props to you for owning it and resetting your direction. That mindset shift — focusing on real BRRRRs that actually move the needle — that’s where wealth gets built.

Keep sharing your journey, man. It’s posts like this that make the rest of us double-check the mirror.

Hey Ansh,

Congrats on locking in that seller-financed deal — getting 6 months of no payments is a solid runway to work with.

For the $35K rehab, you’ve got a few decent options aside from using your own cash:

1. Personal Loan
If your credit is solid and you can get a decent rate, a personal loan could work, especially since it’s a relatively small amount spread over two properties. Just be mindful of the monthly payments and how quickly you can get the units stabilized so the cash flow covers it.

2. 0% Intro Credit Cards / Business Credit
If you're comfortable managing risk, a few investors I know will use 0% intro APR credit cards or business credit lines to float rehab costs. Just make sure you have a clear plan to pay it down before interest kicks in.

3. Private Money
Since you’ve got equity being created with the rehab and no payments due for a while, a private lender might be open to lending short-term against the after-repair value. You could offer a 6-12 month term with a solid return, secured by the property or even unsecured if they trust you.

4. Rehab-Specific Loans
Hard money lenders sometimes fund rehab-only loans (especially if you’ve already locked in the purchase). The rates are higher, but they move fast and are used to these situations. If you’ve got a clear scope of work, you could pitch it as a quick in-and-out deal.

Personally, I’d lean toward private money or a low-interest personal loan, depending on your network and credit — both are faster and more flexible than rehab-specific lending.

Feel free to DM if you want help brainstorming structure — I’ve been down this road and happy to share what’s worked for me.

Yes, it's definitely possible — what you're referring to is called a portfolio loan or sometimes a blanket loan. Instead of getting separate mortgages on each property, a lender can group multiple properties into one loan, secured by the portfolio as a whole.

I've seen this used most commonly by investors who already own a few rentals and want to simplify their payments or pull out equity for more deals (especially when doing BRRRR at scale). The benefit is you often get better terms — like a lower overall interest rate or only one set of closing costs — and it can be easier to manage.

That said, the downside is the properties are cross-collateralized. So if something goes wrong with one, it could affect the others. Not all lenders offer these, but a lot of local portfolio lenders, credit unions, or commercial lenders do.

If you're investing long-term and want to grow faster, it’s worth exploring. I’d start talking to local banks that specialize in investment real estate — they’re usually the ones most open to structuring something like this.

Let me know if you want help thinking through when it makes sense to use one.

Hey Tyler, appreciate you sharing that! I'm over in St. Pete but always looking to connect with other agents and investors across Florida—especially those putting together meetups like that. July 12th sounds interesting, I might try to swing by. Thanks again!

Investor & Property Manager | St. Petersburg, FL

Janet—first off, thank you for your service. And second—you are absolutely not too late to the game.

In fact, your post tells me you’re more ready than a lot of people who do jump in: you've built knowledge, developed a clear "why," have solid credit, savings, VA loan access, and a thoughtful mindset about risk.

I’ve worked with investors across all stages—and here’s how I’d frame your situation:

 You Have Key Advantages:

• W-2 income: Makes financing easier.

• VA entitlement: Zero-down financing on your first few deals, house hack or otherwise.

• Great credit: Unlocks better terms.

• Strong “why”: This is huge for staying the course.

• You’re coachable: You’ve done the education work most never finish.

 You Can Invest Alone—Even If Your Spouse Is Risk-Averse:

Lots of couples go through this. The key is to:

1. Separate your investing vehicle (LLC, trust, etc.) from family assets.

2. Use low-risk entry strategies like:

   • House hacking with a VA loan

   • Buying a small rental in your name through an LLC with liability protection

   • Partnering passively in a deal you’ve fully vetted

You don’t need to go big or fast. One smart, cash-flowing deal changes everything.

 What You Could Do Next:

• Run a live deal analysis with someone local or on BiggerPockets (happy to help with this).

• Consider a duplex or triplex with your VA loan—live in one, rent the rest. Low risk, high control, and great learning experience.

• Join a small joint venture where you’re not the active landlord—especially if your husband’s peace of mind is a factor.

Bottom line: You’re not too late—you’re just early in your personal timeline.

Start with one deal. Then use the momentum. You’ve already done the hard part—preparing your mindset and foundation.

Feel free to reach out if you’d like a second set of eyes on a deal, or just want to talk through a safe entry point that fits your comfort zone.

You're on the right path—keep going!

STR Operator & Property Manager | St. Petersburg, FL

Great question, Alli—this is actually becoming more common with younger investors who want to get ahead and stay flexible.

Here’s how I usually break it down when clients ask this:

 Buying a Primary Residence First

Pros:

• Usually easier financing (lower down payment + better rates)

• Builds personal equity and stability

• No short-term rental headaches

Cons:

• Your home doesn’t produce income

• Limits flexibility if you want to relocate or pivot quickly

• Can slow down your investing goals if it eats up most of your loan eligibility

 Buying an Airbnb First

Pros:

• Property pays for itself (if it cash flows)

• Can accelerate your investing journey

• You’re still building equity—just in a business asset

• You can potentially use it yourself in the off-season (lifestyle + ROI)

Cons:

• More complex financing (may require 15–25% down)

• Short-term rental regulations vary—do your homework

• Requires solid property management, even if you self-manage

 What I’d Recommend:

If the Airbnb deal is in a legal STR zone, looks like it’ll cash flow after all expenses, and you’re okay renting your personal place for a while longer—it can actually be a smarter financial move to start with the Airbnb.

That said, run the numbers carefully (AirDNA is great), and make sure you're not buying something that feels like an investment but doesn’t truly perform.

I've helped others in this exact position weigh both sides—feel free to reach out if you want help stress-testing the numbers or checking on local STR laws in your market.

You’re asking the right questions early. That’s huge.

Investor & Property Manager | St. Petersburg, FL

Great question, Juan—I've worked with a few out-of-country investors, and there are definitely ways to make it work, especially if they partner with the right local support team.

Here are a few things to consider:

 1. Set Up a U.S. Entity or Buy in Personal Name

• Many international investors create a U.S. LLC or LP for liability protection and easier tax reporting.

• Some prefer to buy in their personal name for simplicity, but it depends on the home country’s tax treaty with the U.S.

• A cross-border CPA or tax advisor is essential here—they’ll help avoid double taxation and handle things like FIRPTA.

 2. Financing is Tougher, But Possible

• Foreign nationals can still get loans, but usually need:

  • Larger down payments (25–30%)

  • Higher interest rates

  • Established U.S. bank account or credit file (optional but helpful)

• Some lenders specialize in foreign national loans—DM me if you'd like a list.

 3. Find a Trusted Property Manager or Partner

• Since they won’t be local, having someone on the ground to:

  • Oversee renovations

  • Lease and manage tenants

  • Handle compliance and local regulations

• This makes or breaks the investment for most foreign buyers.

 4. Start with Turnkey or Passive Options

• For a first investment, it’s often easier to go:

  • Turnkey single-family or duplex

  • Partner in a syndication

  • Mid-term rental with solid management

• Keeps things simple while learning the U.S. landscape.

If your relatives are looking at Florida, I’m based in St. Petersburg and happy to walk through some example deals, lender connections, or property management options.

Happy to help however I can!

Investor & Property Manager | St. Petersburg, FL

Great topic, Matthew—this kind of proactive thinking is exactly what separates reactive landlords from strategic investors. While we’re still waiting on concrete legislative language around the Big Beautiful Bill Act, I’ve been having similar conversations with my CPA and legal team about how to stay flexible and prepared.

Here are a few thoughts based on what’s currently being floated:

 Depreciation & Bonus Depreciation

If they phase out or cap bonus depreciation (especially for short-lived assets), it could reshape how we time acquisitions and improvements. I’ve started front-loading rehab plans on current assets to take advantage of current rules before any rollback.

If you’re planning to do a cost segregation study, this might be the year to fast-track it.

 Entity Structure & Flow-Through Scrutiny

I wouldn't be surprised to see pass-through entities face tighter rules—especially for high-income earners using aggressive deductions. That said, entities like LLCs and S-Corps still provide critical liability and operational advantages, so I’m not making structural changes just yet.

What I am doing: having my CPA model out a scenario with higher pass-through taxation, just in case.

 Capital Gains Adjustments

There’s definitely chatter about raising long-term capital gains rates or extending the holding period. For me, that means reassessing planned exits and possibly accelerating sales of low-performing assets this year, especially in states where I'm already facing high tax exposure.

If you're in a strong equity position, it might be time to either sell now or refi and hold long—depending on your market and goals.

 General Strategy

Personally, I’m staying active—but more selective. We’re underwriting with higher exit taxes in mind, and exploring more mid-term rental strategies that create flexibility. Not pausing acquisitions, but being more conscious of holding periods and cash flow resiliency.

Always open to sharing what’s working and learning from others—this is one of those rare moments where staying a few steps ahead could save (or make) you six figures.

Let me know if you want to connect offline about entity strategy or bonus depreciation—we’ve been digging deep on it this quarter.

Thanks, Kyle Wheeler

STR Operator & Property Manager | St. Petersburg, FL

Great question, Melanie—and a super common fork in the road for people considering STRs. The decision between buying a true investment property vs. a second home with STR income depends a lot on how you plan to use it—and how much you want the IRS involved in that definition.

Here’s a quick breakdown to help you compare:

 Option 1: Second Home w/ STR Income

• You stay in the property personally (including friends/family time).

• You can still rent it out, but personal use impacts tax deductions.

• If you use it more than 14 days OR more than 10% of total rental days, it’s considered a personal residence with rental activity under IRS rules.

• Pros:

  • May qualify for second home mortgage rates (usually lower than investment)

  • You get personal use flexibility

• Cons:

  • Rental-related expenses must be prorated based on personal use

  • Less tax write-off potential (can’t take passive loss deductions unless it qualifies as a business)

 Option 2: Pure Investment Property (STR Business)

• You limit or eliminate personal use.

• The property is treated as a rental business under the IRS.

• You can write off:

  • Depreciation

  • Management fees

  • Travel to inspect/manage

  • Supplies, repairs, and more

• Pros:

  • More robust tax benefits

  • Clearer cash flow analysis

  • Easier to grow into multiple units

• Cons:

  • No personal use flexibility without triggering IRS reclassification

  • Often comes with slightly higher lending rates or down payment requirements

 Where to Start:

1. Talk to a STR-friendly CPA – This is huge. They’ll help you map out what’s deductible under each scenario.

2. Run both models side by side (with & without personal use).

3. Use tools like AirDNA or Mashvisor to estimate cash flow.

4. Check local STR rules in Fairplay—some towns in Colorado are getting stricter on licensing.

You can definitely blend lifestyle and investment—it just helps to go in with eyes wide open so you're not surprised come tax time or when evaluating long-term ROI.

Let me know if you want a simple tax comparison spreadsheet—I’ve helped a few folks model out these exact two options.

Thanks, Kyle Wheeler