I did something similar a few years back. I went fully remote while working at a startup and traveled through Asia. While I agree with many points, my experience was more of a mixed bag.

1. Not every job is suitable to do while traveling. Especially if it's kind of unstable like early stage startups. Putting of fires at work on a flaky internet connection while sweating from heat is not that fun and leaves you quite exhausted. It's also hard to plan for anything more serious, if you have to be available when anything breaks.

2. You really need to stay in one place much longer when having a job (2-3 months), as you will have much less free time to enjoy wherever you are.

3. If you work 5 days a week it will limit you excursions into less developed places (with really bad internet) to only 2 days. Quite often these places are what's the best about area you are in.

4. I think going out with expats is not a complete no, no. Just don't do that exclusively. You can get some great tips and avoid many stupid mistakes thanks to other fellow travelers. Especially when you are in a new place that's really different from what you already know.

5. Try to connect with people as much as possible. At the end of the day, that's what you'll remember and what will affect you the most.

I've hacked together an anti procrastination browser plugin which blocks blacklisted pages and displays a dashboard with the alternative actions:

- a todo list - maybe I can do this small chore now?

- a break timer - maybe it's time to break?

- and some simple statistics to shame me into not going through.

If I want to go through for some reason I can solve simple adding task, which is ok when I really need to, but stops me when I am procrastinating.

It's a first version, and one of many such plugins, but it's specifically tailored to my needs. Maybe someone will find it helpful. It's here: https://addons.mozilla.org/pl/firefox/addon/instead/ and here: https://chrome.google.com/webstore/detail/instead/bokgngfmhc...