Not sure where you plan to go, but be warned that "triple" towing is not allowed in all states. You may not be able to tow that extra trailer. I would look at narrowing down tools, as I think most maintenance jobs don't require that full of a tool set, especially as technical jobs require a license (plumbers, electricians, and even gen contractors) which would be difficult (and expensive) to acquire in multiple states.
That being said, I know folks that work for construction companies and travel from job to job living in RV. I remember a couple of families that installed lighting in large buildings, moving every 3-4 months. They worked for a company that subbed for major construction companies.
