I may have missed it, but I don't have a good idea of what remains in the trailer. How big the job of making the unit useable is depends on what needs to be done. Plumbing working? Electrical working? Anyone falling through the floor? Are beds there? I guess what I am saying is that the task of putting the trailer into shape to use may not be the equivalent of doing the full monty right away. Use it, then decide whether you want to go full timing. You can live with knowing some things need fixing as long as you know the trailer is safe and the stuff you need to work does work.
As for supporting yourself while traveling the country, what are the prospects for you and/or your wife doing distance working via computer? Working in software suggests this as a way to make money to support your travel.
Last, working on an AS takes ingenuity, common tools, attention to detail, ability to plan, willingness to learn from mistakes, and patience. The planning skills needed to plan out a software program are the same skills used to work on an AS.
1978 Argosy 6 Metre Minuet
2006 Toyota Tacoma