Not OP, but I have been doing something similar in Airbnbs for three years ( I was interviewed for an article last year: https://qz.com/643181/ ). Sometimes I move between neighborhoods while working on-site in NYC / SF Bay Area, other times I was a traveling consultant, other times I work remotely and choose where I go. Usually I stay 1 month (reaching 2 months at only two places).

It works because I am flexible about renting studio apartments or rooms in Airbnb-dorm-like houses, and I don't have other responsibilities or attachments. Compared to the up-front costs, commitments, and assorted bills connected with an annual lease, I prefer it.