You'll have to read the insurance policy. The fine print on our insurance policy states that pl/pd coverage follows us as long enough it is "legally" hitched. And claim amount is based upon value at time of occurrence.
As far as overhead clearance goes...you have to find out. I hit a tree branch and ripped my awning on a public street, two blocks from my house. No restrictive clearance signs. Called the city, they said to place a claim against them. Filled out a ton of paper work and a ton of pic's of where this branch was and has been hit many times before. Two months later claim is denied because the city has a law that exempted them from their own laws. But they would start a "work order" to trim the tree. No help to me and wrong in my opinion. But that is how it turned out. Reading your posting got me fired up again of how my city says not my fault and not their fault, but started work order. Seven months after hitting branch, still nothing has been done.