All Forum Posts by: Jonathan Dempsey
Jonathan Dempsey has started 20 posts and replied 149 times.
Post: Airbnb in Philadelphia

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey Andrew!
It's so exciting hearing you want to get into the Philly market! As for laws and regulations, I would keep an eye out on CMX-3 zoning changes and any other zoning changes happening in the future.
Also, if you haven't considered it yet I would check out the Poconos as they have less restrictive laws and regulations in place for anyone trying to Airbnb where in Philly it may be a little bit more difficult to keep up with everything.
Live free,
JD
Post: Looking for advice for Airbnb Arbitrage

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey Mike!
I’ve gone from your shoes (figuring out what to buy for my first property in or around Philly), to now 16 properties since I began! I'm so excited to hear you're looking to get into Airbnb in the area, and just wanted to say congratulations on getting started!
Post: Starting in Philadelphia

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey Dylan,
Two areas I would recommend in the Philly area to look out for:
- Point Breeze
- Norris Square
If you'd like to chat more, feel free to shoot me over a DM!
Post: Vacation Rentals in the Poconos

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
@Vic Zav Hey Vic! How does your current portfolio look like, and what has gotten you interested into the Poconos market so far? I'd love to chat more!
Post: Philadelphia Suburbs New Investor

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey Michael!
I’ve gone from your shoes (figuring out what to buy for my first property in or around Philly), to now 16 properties since I began! The journey only becomes more exciting as you get started!
DM me if you would like to talk about all the options you would have, I’d love to talk more!
Live free,
JD
Post: Pocono vacation rental

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey @Amit Kayastha
I recently had a successful launch of 5 properties up in the Poconos. And will be expanding. Would be happy to bounce ideas off each other so we can attack the market together!
DM me if you would like to go over some of the options you have in the Poconos area, I'd love to talk more.
Live free,
JD
Post: Looking for first income property in Philly

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Hey Daniel!
Congrats on looking to purchase your first-income property in Philly!
The fish town area would be a good start! The great part about the Philly market is that you always have other options that can be considered too.
DM me if you want to chat more about the options, and how to get started!
Live free,
JD
Post: Setting up a Short Term Rental

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
Love all the support and prosperity in this thread! I just launched and am growing the footprint in the Poconos as well. Such a cool area with the opportunity to create many great experiences for guests. Would love to connect with you guys and maybe even do a meetup sometime in the next two weeks? If interested PM me and I'll start to put something together central to Pocono Pines and Lake Harmony!
Post: Curious about people's cash flow numbers on STR's...

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
@Kirsten F.
What is the purchase price of the home?
It's important to compare apples to apples. You could look at percents, cash on cash, cap rate or IRR.
But as previously mentioned its not just return, there is the time commitment and coolness factor to every investment. Finding the balance of return / time commitment / coolness factor is what you will need to choose between.
Smaller properties may be heavier cash on cash but will take more of your time, PM or not.
It is possible to find short term rentals that have high ROI and low time commitment if managed properly.
Cheers!
Post: First Property Purchase (Long Term Advice)

- Rental Property Investor
- Pocono Pines, PA
- Posts 152
- Votes 117
@Oscar Zhang
Hey Oscar, congrats on getting into your real estate journey!
As someone who grew up in the suburbs of Philly and began my real estate journey in Philly, I will say theres some great benefits financially to being in the city. Depending on your balance of wanting a future investment versus wanting a place to call home for decades to come, that will change your search. Somewhere you will live for 1-2 years is easier to think financially than somewhere for 5+ years.
With that being said, you will likely have to do some soul searching to find out which neighborhood you most resonate with.
DM me if you want to chat more about the options and how to get started!
I’ve gone from your shoes (figuring out what to buy for my first property in or around Philly), to now 16 properties since I began! The journey only becomes more exciting as you go!!
Live Free,
JD