As a young (55) retiree, let me tell you that you definitely need to think about health insurance. It is EXPENSIVE! and it is something that you definitely need and will be needing more, the older you get.
I don't have any idea about a single guy workamping, but I am sure it is something that can be done.
I hope you find something that works for you.
2017 Ford F350 Crew Cab 6.7L 4x4 DRW