All Forum Posts by: Jorge Vazquez

After over 20 years in real estate, I've learned to listen when the red flags start waving—and this Naples condo is waving a few. I've dealt with properties like this before, and I've even gone through similar situations with my own mom. We had a condo where the HOA turned into a mini-dictatorship overnight—raising fees, changing rules, and making it nearly impossible to rent or sell without drama. It became more stress than it was worth.

Now, looking at your numbers—rising HOAs, insurance, flat appreciation, and only $500 a year in cash flow—you're not getting enough return for the risk or the headache. Even if you paid it off, you'd be parking a chunk of money into an asset that doesn't move the needle and is losing control to the HOA board.

If it were me—and I’ve had to make this same call with my mom—I’d look at selling and reinvesting the capital into a property where you’re in control. A nice single-family in a growing area, something with strong rent demand and better appreciation upside. You don’t want your hard-earned capital trapped in a place where you have no say and no leverage.  I actually wrote an article " the new dictatorships."  good luck.

If you’re just getting started in real estate, let me tell you something from experience:

You don’t need to know everything. You just need the right team behind you.

At Graystone, we work with a lot of new investors—many of whom started just like you. Some with $10K, some with just the courage to take the first step. Now? They’re closing deals, building passive income, and living the life they dreamed of.

Here’s what we provide to help you get there:

✅ Access to off-market deals
✅ Support from real-life investors, not just salespeople
✅ In-house property management and lending
✅ Step-by-step guidance from day one

You don’t need to figure this all out on your own. We’ve got the blueprint—you just need to plug in.

👉 See what we’re all about: https://graystoneig.com/agent/joinus

And if you're ready to talk, schedule a quick chat with me here:
📅 graystoneig.com/ceo

Keep it consistent, stay patient, stay true—if I did it, so can you!
Ready to connect and strategize?
Contact me at graystoneig.com/ceo –
Jorge Vazquez, CEO of Graystone Investment Group & its subsidiary companies, and Coach at Property Profit Academy

Hi Ale — my wife and I were just in Bariloche and absolutely loved it! What a breathtaking place to grow up. Patagonia has that peaceful, untouchable vibe — truly unforgettable.

I’m originally from Puerto Rico and have been in real estate for almost 25 years — licensed broker, wholesaler, and owner of multiple real estate companies. I’m all about the BiggerPockets mission and here to support however I can.

Looking forward to seeing where you take things as CEO — ¡vamos con todo!

– Jorge Vazquez

Hey Ronnie, great to have you here and love that you're exploring the property maintenance space—it’s way more important than people realize. After managing hundreds of units and building a portfolio of nearly 40 rentals, I can tell you the biggest pain point is exactly what you mentioned—chasing vendors for quotes, updates, and timelines. It’s a mess if you don’t build a system.

I always try to build loyalty with a solid vendor bench over time, but yes—I still get multiple quotes when testing someone new or doing big projects. The trick is starting small. Give them a test job. See how they communicate, how they clean up, and if they meet deadlines. Also, if you're tied into a property management company, leverage their vendor network. Those guys usually show up, do the job right, and don’t want to lose the PM’s business.

I saved clients thousands just by knowing which vendors to call and which items don’t need to be replaced. I call it “Tonka thinking”—don’t replace it just because it’s old. Run it until it breaks. You’ll save a ton over time.

If you want to hear more about how I’ve built systems around this and how to turn maintenance into a profit center, happy to share more. Good luck, and keep learning—it’s a valuable lane to be in!

Hey Monique, welcome to the world of real estate. You're already ahead of the game just by asking questions and getting curious. I always tell new investors to start by figuring out how fast you want to grow and how much time you really have. If you're tight on cash or time, house hacking is the easiest and fastest way to get started. You live in the property, rent part of it out, and use that to build your next move. That’s actually how I went from one property to almost 40—with hardly any cash starting out. If you’ve got some savings like 25K, you can also look at rentals in up-and-coming areas. Just pick a strategy that fits your life right now and grow from there. Let me know if you want to bounce ideas around.

Congrats on selling your business—that’s a huge milestone! I’ve been blessed to build a portfolio of nearly 40 properties and run a property management company, a brokerage, and a lending business. Juggling all that plus a marriage hasn’t been easy, but I never aimed to get rich overnight—I just wanted peace of mind no matter what cycle we’re in. My best advice? Give yourself a year to “intern” in real estate. Try different strategies—flips, rentals, short-term, lease options, notes—whatever catches your interest. Once you find what lights you up, get clear on the type of income you want and your long-term goals. I always tell my team: know your last property before buying your first. That’s how you create a real roadmap that fits both your current situation and where you really want to go.

Here to help if you ever want to bounce ideas or review deals.

Hi Brad,

Let me know if you'd like an introduction—I know all the main guys over at Advanta IRA and would be happy to connect you directly. Been working with them for over 20 years and have a few active deals with them right now.

Here if you need anything,

Hey Trace, great questions—and after doing this for 20 years, owning close to 40 properties (a mix of long-term and short-term), and buying my first 10 homes pretty much the same way you’re thinking, I can say your strategy is solid. You’re right that Tampa only allows ADUs in certain zones and usually requires owner occupancy, and STRs under 7 days aren’t allowed in most residential spots. But mid-term and long-term setups still work great if you pick the right area. I’ve helped a ton of out-of-state investors do this, and happy to help!

Christine, Here’s one powerful tip I used to go from 0 to 10+ properties:

Start with house hacking—rent out a room, the in-law suite, the garage, or even the backyard. It’s the simplest way to generate income while living almost rent-free. The hardest part? Convincing your significant other. Trust me, that negotiation was tougher than some of my closings… lol.

But I didn’t stop there.

I also got creative:

• JV'd with people who had the money while I brought the hustle

• Used lease options to buy without big down payments

• Took over properties subject to existing mortgages

• Structured wraparound mortgages to create cash flow from day one

• Worked on novation deals (so I didn’t have to close before assigning)

• And even used property sharing agreements to split equity without going on title

If you don’t have all the cash, that’s okay—just bring the strategy. There are plenty of ways to own real estate if you stop thinking like a tenant and start thinking like an investor.

Hey Thomas—been investing in Florida for over 20 years now, started as a financial advisor before jumping full-time into real estate. Sounds like you’re in a great spot financially, and I love the long-term appreciation play. Just a heads-up though: even with a property manager, rentals aren’t totally set-it-and-forget-it. There’s always a little homework involved—tenants, maintenance calls, insurance stuff, etc. But man, the tax benefits and equity growth make it all worth it if you stay patient. Happy to share what’s worked for me in Tampa if you ever wanna compare notes.

—Jorge