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All Forum Posts by: Jonathan Dempsey

Jonathan Dempsey has started 20 posts and replied 149 times.

Post: Starting out in House Hacking - Looking to Connect!

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Jun Ho Lee!

House hacking is the way to go if you are just getting started! If you ever need anything don't hesitate at all to reach out! Best of luck! 


Live Free,

JD

Post: Need help with first deal!

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Couldn't agree more with @Sherry Patterson

Never limit yourself and consistently educate yourself @Andy Ronquillo

Best of luck, and reach out if you ever need anything! 

Live Free, 

JD

Post: Financing STR out of college

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Jake Greener

Have you considered house-hacking yet? This way you can qualify for an FHA loan and only have to put 3.5% down and will have some extra money to improve the property.

Always happy to help! Feel free to reach out whenever. 

Live Free, 

JD

Post: Should I sell a long term rental to purchase a short term rental?

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Jessica Finkbiner

I would consider diversifying so you can see what works best for you! Ever since I had gotten into the STR market I haven't thought about having any LTRs! Best of luck, and hope all goes well for you!

If you ever need anything, don't hesitate to reach out! 

Live Free, 

JD

Post: PMS what software do you use?

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Curtis Naugle

You won't need software for one property. I would give your guests your phone number then they can easily be in contact with you for now. 

In the meantime, as you start to scale I would start evaluating your options and testing out which software would be most suitable for you. 

There are several out there like Guesty, Breezeway, and Hospitable. You choose what works best for you! 

Always happy to help! 

Live Free,

JD 

Post: Allow me to introduce myself

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Ryan Johnston

Welcome to Biggerpockets! If I can ever help in any way don't hesitate to reach out. Best of wishes! 

Live Free, 

JD

Post: Multi-family Investing in Pennsylvania

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Angelito Mamutuk

Feel free to reach out whenever! Always happy to help out man! 

Live Free, 

JD

Post: Multi-family Investing in Pennsylvania

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Angelito Mamutuk, if you are looking for multi-family opportunities I would look into urban areas. My recommendation for an area with a greater amount of inventory would be Philadelphia, especially since the shoulder season is upon us. 

Like you had mentioned - the Poconos will have more STR and SFR options. Although I wouldn't count this out on your search, as recently I've had a successful launch in the Poconos and have seen high rental rates ever since.

Always happy to help, don't hesitate to reach out at all! 

Live Free, 

JD

Post: New Investor looking to network and connect!!

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Jesenia Matias, congratulations to you and your fiance for getting started on your journey towards financial freedom. Don't hesitate to reach out if you guys ever need anything! Best of luck! 

Live Free, 

JD

Post: Philadelphia Multifamily Investing

Jonathan Dempsey
Agent
Property Manager
Posted
  • Rental Property Investor
  • Pocono Pines, PA
  • Posts 152
  • Votes 117

Hey @Joe White, I'm in the Philadelphia area and my portfolio mainly consists of Short-Term Rentals. If I can ever help in any way, please don't hesitate to reach out!