Overall the shingles look pretty good to me, no discoloration or cracking. I say you have a quite a few more years out of it. Wind will rip a shingle up quick if it`s strong enough, even a small 30-40mph gust will take a loose shingle up. In the colder months they tend to be stiffer than summer when the sun is beating down on them, so if it was colder when the winds came thru that would explain alot.

As far as the slight mold on the siding, that`s just nature! There is no reason for them to give you grief about that other than to be ahole`s.