I have heard good things about the Flex-Seal type of rubberized paint as far as sealing leaks.
I would use two layers of
Reflectix for insulation. It's easy to work with and pretty cheap. If you want to get fancy use some foam insulation material to make an air gap between the layers. Tape should hold it in place while you rivet.
There's no way I would ever put that pink fiberglass back into one of these trailers. I just removed the front half of my belly pan and that stuff gets pretty nasty....
John