So this is what I meant by things are getting exciting. We had a big and terrible snowstorm on Valentine's day and water dripped from the ceiling for three days afterward. This is what the wall looks like now:You can see that we still have some moisture issues where the wall meets the ceiling, so we are going to have to take care of that before the new plaster goes up. The insurance adjuster diagnosed the problem as ice damming, and he didn't think there was any damage to the roof, but I'm not sure he was 100% right.
We had been planning a renovation of the kitchen for some nebulous time in the future when we will have tons of extra money, but this hole is kind of forcing the issue. The water damage is conveniently located where we would like to add a range hood, so at least that's helpful.
We have a sort of related issue with the ceiling in the rest of the kitchen. There's no water damage there, but it looks like this:
Notice the funky faux medallion treatment around the ugliest fixture ever? And the weird texture covering the rest of the ceiling? I want to move the fixture so it is centered over the island, so the ceiling is going to have to be smoothed out. I am still trying to figure the best way to accomplish this with my own minimal DIY talents.