@Jonathan R McLaughlin I'm looking in the 5 college area, Shelburne Falls out to Colrain and Charlemont, and Berkshire County. My son lives in North Adams. I live in my hometown of Hingham and I rent, sharing a 3 bedroom house with a family member at a townie price. Great situation because he is happy to split the bills but also likes the idea of having the place to himself. So I can move out whenever I want. Totally priced out of the South Shore market. Prices are insane here. $400,000-$500,000 for an 800 SF house. I poke at Vermont a lot and Maine a little but it's a bit futile because of quarantine requirements. You have to get something under contract to be allowed to go see it. I did the free 'subscription' to Airdna. Sheffield, Great Barrington, Lenox and Stockbridge in Massachusetts and Stowe, Morrisville, Manchester Center, Woodstock and White River Junction in Vermont all have $3079 - $4098 monthly average short term revenue (not gross) with 45% - 73% occupancy all depending on which town. The average unit size is generally a 3 BR. Of course those towns are generally more expensive to buy in. I wouldn't consider an airbnb in a town with less than $3000 monthly revenue because the costs of running an airbnb are high. I have also been starting to look at markets in other places in the country, mainly in the Smoky Mountains of Tennessee, since that's a thing, but I am finding myself balking at buying a property I can't hop in a car and drive to within a few hours. I guess I want the insurance that if I screw up and my first deal is a flop, I can at least move in to it and not pay rent or another mortgage somewhere else. I am certain that I want to live in New England. You hit the nail on the head saying airbnbs aren't a conservative investment. I am a born risk taker that has been though some challenges and tragedies that made me much more cautious. So I can skew in either direction. I'm excited to explore this avenue as it feels like coming home to my true nature of being willing to take risks, think outside of the box and try new things.