Picked a 6-month lease over month-to-month, no regrets so far
Everyone in the nomad groups keeps pushing month-to-month rentals for flexibility, but I went with a 6-month lease in Medellin last January. It cost me $450 less per month than the flex option, and having that fixed base forced me to actually plan my travel instead of bouncing every 3 weeks. I still work remotely and take weekend trips, but I don't waste half my day hunting for new Airbnbs. Has anyone else found that longer commitments help them focus more on work than the constant moving?
I did the opposite once. Signed a year lease in Lisbon and ended up flying home after 4 months because of a family thing. Had to eat 8 months of rent. That one hurt. But I get the focus part. When I was bouncing around every few weeks I spent way too much time reading reviews and checking bus schedules. Now I just pick a place, stay put, and actually get my work done.