I started doing this back before Remote was really a thing. So initially, I'd work short 3-6 month contracts on-site in the 'states with 9-12 month stints of travelling in between.
Eventually, as it became more possible, I started lugging a laptop along and doing client work from the beach on rest days from climbing. I'd sometimes stop in one place for a month or so just to go heads down for a client or on my own project stuff.
In 2011, I took a full-time contract for a fully remote company in the 'states, while living in England. I was their furthest "remote" employee at the time, though they quickly started hiring more once they realized that it worked. There were guys on the team working poolside while digital nomadding around the world by the time I left 5 years later.
France happened after a long search to find a good surf break to set up shop at. The issue there is that surf always happens right next to the beach, where they keep all the $5M houses. Or in places full of grumpy expat American surfers that we decided we didn't want to be our sole source of potential friends.
Climbers, on the other hand, don't get grumpy and territorial over climbing areas. They're just generally lots of fun to be around, so the only real trick is to find a place that you won't climb out. Most crags have only a few hundred routes at the level you'll be operating at (even factoring in improvement from living next to said crag), so lots of cool places (including Tonsai beach iteslf) got ruled out on those grounds. Font, however, has 30,000 problems recorded and new 7th grade lines going up at the rate of about one every 3 days. It'll be tough to catch up.
As to living, it works itself out. They have doctors, grocery stores and schools everywhere in the world. Do what the locals do and you'll be fine.
Hope to see you out here one of these days!
EDIT: It occurs that I actually wrote a whole article on this once. Shoulda just linked it:
https://expatsoftware.com/articles/guy-on-the-beach-with-a-l...