Had my last trailer for 8 years, not half as well built as the Escape. In that time, other then yearly maintenance issues and not including the roof leak that took out the floor, I only had my converter go bad. Cost about $200 to self replace. For $752/year I'd self insure.
The floor would have run about $3k to replace, I did it myself for $400 and 3 weeks worth of time. Even had I paid $3k, I would have come out ahead using your insurance figure.