Except for obligations put on me by family, and stuff like cruises and international tours, I quit planning at retirement. When I have free time, and not projects, I just go. If full timing, I would just go, with the general principle that I want to be where I can keep the windows open most of the time and not run either furnace or air conditioning.
Bills can be checked and paid online, an except for jury duty summons and the forms I need to file income tax (which come at a specific time) the rest is just junk mail accumulating in my P.O. box. I'll take off for two to six weeks at a time, mail coming to the house (junk, license renewal forms or jury duty summons) goes on hold until pickup, P.O. box accumulates.
If you are actually full-timing, all your mail needs to be going to a forwarding service, and you can arrange for that to be held until you tell them a new place to send it.