Thanks everyone. We really appreciate your advice and feedback.
We have decided to have the dealer repair the roof of the TT. We will use the big insurance check to pay down the trailer and then will sell it ourselves. We'll ask about $9k, accept $7k, and anything more than $5k is more than the dealer was giving us.
We bought a 5th wheel today that will fit our growing family and we are very excited about it. We'll pick it up next weekend and be ready for Memorial Day! I'm also instituting a new rule: No backing up the rig without a spotter. :)
Happy camping!