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All Forum Posts by: John O'Leary

John O'Leary has started 27 posts and replied 661 times.

Post: New to Site

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

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
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

Hi John,

What market are you in?

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

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

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
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

Classifieds or buying and selling real estate .

Post: New BRRR Investor

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

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
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

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

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

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

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

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

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

Hi Joe,
We’ve worked with several PadSplit investors to secure financing, and while these properties cash flow really really well, they do come with challenges—tenant turnover/issues and being the biggest ones.

One hurdle we've seen is that getting financing can be tricky since PadSplit rentals are still considered non-conforming by most lenders. Many traditional banks won't touch them, and even DSCR lenders will avoid them if the build out is done prior the securing long term debt. That said, we've been able to help investors secure creative financing solutions that work for this model.

If you decide to move forward, just make sure your financing strategy aligns with your long-term goals, and the properties are good fits for Padsplits model. 

Post: New REI - Charleston SC

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

Welcome to BP Tara, and congrats on taking action and joining a like minded community. 

Post: Reconnecting with the BP Community

John O'Leary
Posted
  • Lender
  • Winter Park, FL
  • Posts 700
  • Votes 395

@Tony Thomas @Shawn McCormick I'm in Orlando also. Always looking to connect with other local investors, realtors, etc.