Another reason moving around a lot is always going to be a painful because your address, you being known to be available at a location, is important for legal and financial purposes for lots of service suppliers. Any kind of ongoing transaction will be made difficult by history of moving around a lot.
If you're staying in the same city like he is, all you need is a fixed mailing address. Even moving between cities you can use a mail forwarding service (paying a friend you can trust would probably be better than a commercial service).
You can work around this with a mail-forwarding address, some vendors also scan your mail so you can look at it online and even deposit checks. Lots of RVers seem to be using this.
