My damage estimate would include new roofing for that entire side of the garage, if not the whole garage, as new shingles won't match existing. It would also include money for removing the tree from the roof, putting temporary cover on the roof, chopping up and disposing of the tree. Oh, and replacement of the tree! That tree could be worth 2K.
I once had a neighbor who crashed through my front fence and knocked down a small tree and ran over some potted plants. Wasn't even her fault. Other guy took off. Her insurance paid me just short of 10K because I itemized everything carefully. Took a year to settle, but worth doing.