My wife and I are looking into investing in short term rentals in vacation markets surrounding NYC (Catskills, Adirondacks, Poconos, etc) and just wanted to check if anyone here might have some insights they could share.

In any building that allows short term rentals, you will have a majority of the owners doing STR. 

First unit lease is up for renewal on 10/31/2024 and has a good long term tenant.

Total cost significantly below their current monthly rent.3- If you have to 'give them' to the current tenant to get them off your books then do if it makes sense long term.  4- Don't do purchase contracts longer than 18   months. 

So, I am allowed to do the 150’ expansion, as long as it accommodates ingress/egress.  

During this year, I've experienced inheriting a crooked property manager I let go on day 1 that tried collecting rents from tenants weeks after, an eviction (same person) and a successful lawsuit against a non performing seller that backed out the day of closing. 

Have your terms together on what type of return youre looking to get.....I would pitch this at a REIA meetup and funds....

How are long term rentals doing?

Terms should include interest rates, repayment schedules, and contingencies for unexpected issues.

If you give them a shorter term lease, do it at a higher rent as you are going to be inconvenienced trying to find a new tenant at what may be a hard time of year.