Vacation/Airbnb Home as a Second Step

[Daniel Moreno]

We live in Boston, and will be traveling to NYC (midtown) every weekend for the next year (Sept-May), and every other weekend for the next 5-6 years. 

We currently run an Airbnb out of our home, which generates good cash flow, and love doing it. 

Would anybody have any suggestions on how we could satisfy both the need for housing on the weekend, and an investment? I'm aware that NYC is tough on running airbnb's and that co-op's are tough to work with. Are there areas within an hour or hour 1/2 or so that would be a good place to start looking?  We're open to just about anything-condos, studios, cabins, or vacation homes. I was thinking of an area that is popular in summer and winter.

Alternatively, I was thinking of a summer/winter home somewhere in New England, that would generate enough to help off-set the cost of travel.

We have about 150k in home equity and 25k in cash, although we can maybe come up with more (10-15k) in the coming months.

[Mohammed Rahman]

Hey @Daniel Moreno - my perspective is your best bet would be a modestly priced multifamily property in either Queens or Brooklyn. It depends on where you need to be while traveling to the city, but both of those boroughs have an easy public transport connection to Manhattan. 

I recommend these areas in Queens for decently priced multifamilies (2-3 units) that you can rent out partially or fully depending on which route you go: Elmont, Richmond Hill, Jamaica (north, not South). 

Shoot me a DM if you'd like to connect, I have friends that study in Boston and have been back and forth a few times - I'm also an agent & investor, happy to directly help or at least point you in the right direction. 

[Lien Vuong]

Something in Hudson Valley? That’s a great year round destination for New Yorkers and commutable for you. 

[Tom Wagner]

Agree with Lien on the Hudson Valley, but proceed very cautiously as towns are constantly changing their Airbnb laws (especially as prices continue to rise). You also could consider a property in Jersey City, but their Airbnb law changed recently so you would need to buy a 2-unit property and rent the other unit to a long-term tenant who would be willing to serve as your "on-site property manager.

[Jarrod Kohl]

If you are going Boston to NYC you could also look at places in CT/Western MA or similar. 

Depending on where in Boston you are, we have also had great luck doing Airbnbs on the Cape. While it is certainly Seasonally summer. We still had more than enough revenue to profit in the offseason. 

[Charles Renn]

Hi @Daniel Moreno,

Welcome to BiggerPockets! Thanks for sharing your situation. I've been looking in the Poconos for a few reasons, but the primary reason is the established STR regulations. If you'd like a referral for a local agent, let me know. Best of luck!