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.