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All Forum Posts by: John O'Leary

John O'Leary has started 28 posts and replied 674 times.

Post: Beginner Seeking Tips on Getting Started in Real Estate Investing

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Hello Haneef, 

First off, congratulations on finishing school! That’s an enormous achievement, and I wish you all the best as you start your real estate journey. Building a team from the beginning is key. As a new investor, don’t try to be an expert at everything right out of the gate. Instead, focus on assembling a few key people who can fill the gaps—such as a trusted agent, contractor, and local property management expert etc. By surrounding yourself with the right team, you’ll be able to tackle challenges much more effectively. Also, it’s important to have a specific strategy when starting. You don’t need to tackle every avenue of real estate right away—be clear about your goals, whether it’s single-family flips, rentals, or another niche in your local market. Starting with a focused strategy will give you direction and prevent overwhelm. And most importantly, take action. Many people have the desire to start but fall short because they never make that first move. Don’t get trapped in the learning phase for too long—take initiative, even if it’s just one small step at a time. The real growth happens once you take action. Good luck, and I’m sure you’ll find success with the right mindset and approach! Keep us posted on your progress

Post: Recommendation for a General contractor (GC)

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Try Homeadvisor. It might be difficult to get someone to offer up their GC if they do a good job since reliable contractors are tough to find and retain. 

Post: Kissimmee Florida STR advice/property management

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Hi Tim,

I'm in Orlando and have a client with a substantial STR portfolio in CF, including about 15 properties in Kissimmee. They also manage additional STRs for local operators. Please feel free to reach out if you'd like to discuss further.

Post: New to Site

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Hi Erik!

Welcome to BP, and I doubt it was all luck. I'm in Orlando and happy to connect.

Post: How many of you are planning to sell your STR property?

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Hi John,

What market are you in?

Post: Off market and fix and flip - Team Building & Advice

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

While I am a lender, I personally use hard money on all of my own investment projects. Leverage, when used correctly, is one of the most effective ways to scale. The key is vetting your lender properly—asking the right questions, understanding the terms, and ensuring the numbers make sense for your strategy. While using financing does mean I don't keep 100% of the profit due to borrowing costs, it allows me to take on multiple projects at once and operate in higher price ranges than if I were only using my own capital. If you're strictly buying turnkey properties and financing with DSCR loans, keep in mind that you'll typically need to put down 20% or more, and because of the higher LTV, you'll often get the highest interest rate available for your credit bracket. Every investor has a different approach, but I personally buy my rentals the same way I buy my flips..at a deep discount using hard/private money, then refinance with a rate-and-term loan to secure a lowest interest rate.

Ultimately, it comes down to your goals, risk tolerance, and ability to find value-add opportunities. Sounds like you’ve put in the work to build a solid foundation—wishing you success as you take the next steps!

Post: I haven't been on BiggerPockets for awhile, so where can I post a house I'm selling?

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Classifieds or buying and selling real estate .

Post: New BRRR Investor

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Welcome Rob!!

Congrats on taking action and networking within the community! One key piece of advice is to make sure to build strong team around you. RE Agents/wholesalers, insurance agents, title companies, contractors, lenders etc. Also fully understand the refinance guidelines for any DSCR, or Traditional loan products you BRRRR into. Every lender has different criteria when it comes to seasoning periods, LTV limits, and DSCR requirements, so knowing those details upfront can help you structure your deals more effectively.

Looking forward to seeing how your BRRRR journey unfolds. Good Luck!

Post: Anyone personally have feedback on pad split as a host

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

@Joe S. I resent the message, check your inbox. 

Post: Anyone personally have feedback on pad split as a host

John O'Leary
#2 Wholesaling Contributor
Posted
  • Lender
  • Winter Park, FL
  • Posts 713
  • Votes 401

Yes, I'll shoot a DM. It's not bringing her up.