I mounted my carrier on the back bumper of our travel trailer. Works fine, but you can't see it when driving, so I add a few extra bungees just to be safe, and check it fairly often (only takes a second to run back for a glance at a stop sign).
Finding new roads to ride is the fun part...I generally google up a route or two ahead of time to get started and then pay attention as we drive in for cool looking stuff to hit.
I bring along most minor stuff as far as maintenance goes, but if something happens and I am forced to drink beer by the fire for the rest of the weekend, I am OK with that.
I do not do anything extra with insurance. I keep my bike in the trailer for the most part when not riding.