All Forum Posts by: Jonathan Dempsey

Arbitrage seems to be the hot strategy versus traditional short term rentals.

Do benefits of scaling quick without dealing with lenders or too much cash outlay outweigh the perks of down payment and appreciation?

In a vacuum I am team own it, but do both as every opportunity is situational.

Would love to see where the Bigger Pockets crowd lands on arbitrage versus owning! I have a hunch its going to be a one sided assault

Cheers!

@Hal Wilkerson

I couldn't agree more.   Appreciate the perspective you bring here.  Better to get a glimpse at the conservative numbers than to try to make assumptions otherwise.

@Kaitlyn Castillo

Short term rentals are high cashflow relative to any other REI, especially if you self manage to start. There is nothing passive about them unless you use a property manager. Even if you use all the best automative procedures, unless you have a CEO or small operation with a handful of properties, you will need to put a significant amount of time into your business.

It is very much like operating a hotel. Just with all the rooms being in different places!

@Chrisovalantis Boutsikos

Philadelphia and the Poconos are both great options from NY. Not too far, yet affordable.

There are plenty of great books on how to invest from a distance (and this distance is modest).

@Kaylee Walterbach can you be sure to link the article here when it comes out?

@Andrew Bowden

Welcome to the game Andrew! Its a wonderful world

Congrats and thanks for your service!

The best part of short term rental is seeing the vision and design come to life! And I suppose cashflow is pretty cool too. So excited for you to be getting started.

If you want to bounce ideas off each other, would be happy to chat! I operate over 100 units in 4 different cities, and am exploring the Poconos / Cabin market as we speak.

Cheer and best of luck on your launch! Be sure to share your listing with us!

Since the beginning of the pandemic we have seen a massive shift to the suburban/rural markets from major cities.

What kinds of shifts are you seeing / anticipating in your urban market?

Here in Philadelphia, things are returning to normal socially. Housing demand is becoming healthy again. Supply is low and will remain low with the high costs of lumber and other resources associated with construction.

I anticipate a surge in city prices over the next 6-12 months based on these factors.

What is the sentiment in other urban markets?

The short term rental market has been a place of tenacity fueled by promise.  The unfavorable circumstances during the pandemic lead to a significant decrease in available rentals in the market of Philadelphia.  Record travel and social demand will lead to the largest window of opportunity in vacation rental history.

I totally agree @David Luu.  Pacaso could open itself with a broader market if they were to expand the amount of shares.  Surprisingly it seems like they aren't having much trouble gaining traction with their current model.   It would be easy to flex the days available for rental by buying shares or just paying for additional nights.  Pacaso's main incentives are a markup on the sale price when creating the fractional shares, a furnishing fee, and ongoing management fee.  Alot of dimes here and there.  I don't see it being difficult for them to break down the share amount.

Cloud Castle is much more up the alley of investing. The investor dream version of Pacaso. However, like you said it is limited. They seem to be at a point where they need to scale quick and gain momentum. I also don't like how there are no projected returns or explanations of the equity. The concept is incredible, and they did an amazing job with the development and clarity throughout their process. Which makes it more frustrating that they are vague on projections and equity purchasing. My assumption with their lack of disclosure is that they are leveraging and then having investors pay in at a different equity LTV, ultimately consuming more leverage and upside for themselves. Hard to say.