All Forum Posts by: Jonathan Dempsey
Jonathan Dempsey has started 20 posts and replied 149 times.
Post: Amazing 43 unit Poconos Deal
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
I always look at zoning in this market. Not much more interesting than where the short term rental industry is trending with an ever present creative & cashflowing landscape!
Post: Current Philly Airbnb Climate
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
It has been really interesting to see the timing of the pushback on regulations. Regulations came in quick (although there were talks looming). The pushback to January was abrupt. It will be interesting to see how the saga continues.
Prepping for the worst but hoping for the best. With the 2026 World Cup being set in Philadelphia, any precedent set will be huge. Further, Philadelphia is not the first city to see regulation and surely will not be the last. In the ever changing STR landscape, it is becoming increasing valuable to be aware of zoning.
My firm has exclusively been locking up resort zoned properties. We have a large BRRR deal in the Poconos and another modest deal in North Carolina. Happy to share numbers and talk STRs in the PMs. Keep crushing everyone!
Post: Philadelphia Investor Meetup - All Are Welcome
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Putting this back into the spotlight for everyone! Excited to get into the thick of different real estate ventures tomorrow night!
JD
Post: Philadelphia Investor Meetup - All Are Welcome
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hello Philadelphia,
The Live Free team is hosting an investor meet-up & networking event that all are welcome to. At the event you will be able to meet fellow investors, agents, and other service providers. We will break out into groups to discuss what kind of investments we've made, are currently looking at, problems we're facing, and attack the solutions with the help of our peers!
The Live Free Team is made up of a handful of investors with a 25 unit portfolio in Philadelphia, the Poconos, and even Hawaii!
Comment in the thread if we can expect to see you there!
Live Free,
JD
PS - See you there next week...@Tyler Winget @Mike Eichler @Gunner Winget @Joshua Messinger
Post: Rental Arbitrage for Short-Term and Mid-Term Rental
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Quote from @Andrew Garcia:
Hi @Christopher Murphy, first, thank you for the bio. I love when people share a little personality. I, too, am a young guy but I am on the lending side of the business.
With that being said, I agree with you, many lenders are terrible. Since you are quitting your current W2, you should look into DSCR options for future real estate endeavors. It does have a higher interest rate but it has far fewer restrictions.
There are a few issues with rental arbitrage:
1. Many landlords do not allow it.
2. Many jurisdictions do not allow it.
3. Your landlord or jurisdiction may allow it now but may change their mind at any point.
4. Lack of equity growth.
5. Uncertainty. You might not make enough to cover rent for one month and need to come out of pocket or an STR tenant might cause damage to the property that causes you lots of money.
As long as you plan for these and are prepared for the risks, you should be fine with this strategy.
Seller financing is a better long-term play since you get equity growth, stronger certainty when it comes to legislation, no uncertainty with landlords, etc.
You seem like you are well on your way to a real estate empire. Would love to connect!
What Andrew listed out here is exactly what I was thinking. Arbitrage is more hyped up than it out to be by the "gurus". I believe the market for arbitrage slowed down and became oversaturated. There are still opportunities, even then they lack the benefits of ownership. Seller financing is the recipe to make a would-be arbitrage more attractive.
I encourage you to find a way to get into your first purchase. It will change your life!
Post: Vacation Rental Properties
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey @Kelvin John Bio!
I recently had a successful launch with my first unit in Honolulu.
If I can ever help you with anything please don't hesitate to reach out. Best of wishes!
Live Free,
JD
Post: Buy & Hold Multi Unit Vacation Rental
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Great work! @Samantha McEntire
If I can ever help with anything don't hesitate to reach out at all!
Live Free,
JD
Post: New Member Introduction
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey @Michael King!
Welcome to Biggerpockets and best of luck moving forward! My best advice would be to really take advantage of the amazing community BP has, and all of the information that has been posted on the forums in the past.
Best of wishes!
Live Free,
JD
Post: Can renters Airbnb a rental property?
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey @Benjamin Dougherty!
There must be a provision in the lease that states you are allowed to sublet the property out to other tenants. Otherwise, you are not allowed.
Another thing that you must check for is that the area you are in allows short-term rentals, as every single township has different rules and regulations around STRs - A simple call to your township manager can solve this question!
If you ever need anything feel free to reach out whenever!
Live Free,
JD
Post: Airbnb in big bear Need a property manager
- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey @DongHui Patel!
Just like @John Underwood had said - I would try self-managing your property for the time-being and if that doesn't work out then switch to a PM.
Best of luck! Feel free to reach out if you ever need anything!
Live Free,
JD