All Forum Posts by: Matt Jones

I'd second what Bryce said and add that if you receive orders earlier than expected—even just to Whiting Field—you can often use your VA loan again in less than a year. I've worked with many military buyers who purchased a 1–4 unit property here in Pensacola while stationed at NAS, and then used their VA eligibility again 8–9 months later to buy another home in Milton or Corpus Christi.

The VA loan is a powerful benefit, especially when relocation is part of the job. Orders to a new duty station can accelerate your ability to use it again sooner than many realize. If you ever need help navigating that locally, I'm always happy to be a resource.

Hi @Dolores H.
The silver lining is that Pensacola Beach has appreciated really well since 2019, so you likely have some solid equity to work with no matter which path you take.

A few quick thoughts on the three options you’re considering:

1. Selling the condo – This could be a smart move, especially if it’s currently causing financial strain and you’re looking to reset. With the appreciation we’ve seen, you should walk away with good equity, and even in a slower overall market, beach condos are holding their value fairly well.

2. Switching to a long-term rental and managing it yourself – This option might offer more predictable income and lower vacancy, but long-term rental rates on the beach typically don’t come close to covering the same expenses that a short-term rental can—even after factoring in management fees. That said, if you’re open to self-managing a short-term rental, that’s where you’d likely see the biggest financial improvement. Self-management can boost your net income quite a bit, especially with a strong local cleaner and handyman on your team. It’s definitely more hands-on, but might be worth considering given your long-term goal of working in real estate.

3. Pulling out equity to cover other debts – This could create more breathing room now, but it also raises your monthly expenses and may worsen the cash flow situation if the rental income doesn’t increase. It could also limit your flexibility with the property in the future.

I'm based in Pensacola and work regularly on Pensacola Beach, both in real estate sales and property management. I also own and self-manage a short-term rental out there, so I’m familiar with the unique challenges and opportunities the area presents. If you ever want a rough idea of your condo’s current market value or potential long-term rental income, feel free to message me—happy to help however I can.

Welcome RJ!  What kind of investing will you be doing and are you focusing on any particular areas down here?

Welcome, Jay! Pensacola’s a great market for investing, and there are a few different strategies that work well here. Are you planning to do long-term buy and hold?

There are a couple of local investor meetups you can plug into, and of course BiggerPockets is always a solid resource too.

When it comes to knowing if you’ve found the “right first one,” I think it helps to get pretty specific with your criteria and then really watch the market for anything that fits. If your criteria is dialed in and you're keeping an eye on new listings and what things are actually selling for, you'll be in a good spot to recognize a deal when it hits—and feel more confident making an offer.

Hope that helps—good luck getting started!

Sent you a message

Hi Jami,

I buy multifamily properties and, as a local real estate agent, I represent buyers who buy multi and single family properties.  Feel free to add me to your distribution list.  

When was it built, and how old are the major systems? $3,200 is probably a decent rate unless it’s new construction. New construction properties can qualify for significant insurance discounts, but otherwise, I generally expect insurance in this area to run a little over 1% of the property’s value if it’s in decent condition.

Feel free to DM me if you’d like a good insurance contact to shop around for a better rate. Just a heads-up: with the way the insurance market has been here over the past couple of years, this is accurate as of today, but things could look very different (for better or worse) in 6+ months.

 Welcome Terrence!  Pensacola is a great market for investing and the number of properties available right now is up so there are actually some on market properties with potential.  We have lots of wholesalers so I'd recommend getting on their lists to add to the number of investment opportunities that are coming across your plate.  PM me if you need a list.  I'm also happy to share access to a spreadsheet where I track Single Family, Multifamily & Rental Inventory for the Pensacola Market(Escambia & Santa Rosa Counties) each week.  Good luck & let me know if i can help you with anything!

Hey @Joel Matthews,

If you decide to invest in multifamily closer to home shoot meet a message.  I specialize in small multifamily properties in Escambia & Santa Rosa counties.