This weather just sucks. LOL "fix" There's probably going to be a lot of that going on. So far my vents at work have stayed on, one blew off a few years ago and I had to climb up on the roof to put it back on. Nailed that sucker back down and put tar around the edges to prevent any leaking.
Your roof looks weird. It looks like it has 4 or 6 inch wide planks instead of sheets of wood. Looks like there was actual tar put down then the shingles on top of that.
There was a funnel cloud that went through like 3 years ago that tore some of the roof off there, so it was tarred before, maybe that's what you're seeing?