One of the things about freestyle travel is that you never know what you are getting next. We ate dinner in a ski resort/brewery. I’ve been skiing enough to know that you avoid places like this (in season or out). We stayed in one Airbnb in a terrible (but up and coming) neighborhood.
We stayed in a lovely place in Lenox. It’s part of the adventure. It’s nice if things are predictable. And I hate it when my guess/choice is not ideal. It always seems to work out. SFSG (so far so good) It helps to have an understanding travel companion….because and up and coming neighborhood looks pretty threatening in the dark of the night. Anything tends to look better with a little daylight.