My first thought is per the difference between a fiver and a trailer: either one (of any size) will require the purchase of a truck, so that's sort of a non-issue financially speaking except maybe for size-of-truck.
Since you already have a (paid for?) vehicle you could tow behind a motorhome, that might be the best option for you. This especially since it sounds like you're going to be staying in one place for awhile at a time...it would be more expensive to use a truck as a daily driver during your stays than to use whatever car you now have, assuming it's a relatively small one.
Per what insurance will cover: that depends a lot on what kind of rig/insurance you buy.
I for one see no difficulty with staying in touch with your work- can't one buy some kind of internet access that follows wherever you go?