My garage is ninety years old or so, and has had rolled roofing applied several times, but recently I lost part of it to winds, and my last roofer said that it shoud be entirely redone due to the condition of the decking boards, etc. Well, I can't afford a new roof, and the garage also leans a bit--has done that since I bought the house in '87, and it hasn't moved since--so I can't sink a lot of money into it.

My question is this: would an elastomeric coating seal up the roof, if I use something like the self-sealing ice membrane for the larger leaks underneath first?

If I had the insurance company come out to see the garage, would they pay to have it rebuilt, without a claim having been made?