I've been in tech for about twelve years working in full-stack web development, DevOps, and a bit of ML. I also have a few years experience in management. I don't really know how to begin looking for these sorts of roles, so I'm hoping folks here have some experience and could share some pointers.
Any input is appreciated!
1) Wellfound (previously Angelist) can sort job ads by location Remote.
2) Once you get a remote position the employer won't care where you are as far as you do your job on time, having an internet connection and be available on the timezone of the employer is good enough for remote jobs
3) Moving more often than 3 months actually turns into a vacation with little working. I recommend to not move too fast. You can easily get visas for 90 days and stay the 90 days in one city. Some famous places for digital nomads are:
Chiang Mai, Thailand Medellin, Colombia Valencia, Spain Budapest, Hungary
but of course there is a ton more: https://nomadlist.com