One of my subcontractors did van life. He was the hardest to work with:

1. He had a refurbed van that was always breaking down so he was always working on it rather than on the work I needed done
2. He wasn't always in data/wifi range. He wouldn't know the situation in advance so I'd never know when he was avail.
3. He went through crazy weather and was often just surviving the weather rather than being able to work
4. Got sick a lot. See #3.
5. He couldn't always find places to park overnight, so a lot of his time was spent on that.

I'm sure it can be done, but it def doesn't seem as easy to me as going to one spot with good wifi for a while.