So the contractor is in his mid 60s, and the guy doing the capping is 68 years old. They were recommended as really experienced and honest as it comes, and have been doing it for 30+ years. I was suspicious about the hospital thing too but I'm gonna give them the benefit of the doubt. It's not like he's off doing other work since his brake is still in my driveway. When they get back to it, the old capping (full perimeter) is going to be removed and redone.
As far as the wrong size windows, I was there when he measured and all were nominally 30" wide, but the upstairs windows came in at 39" wide. He said that he went back and forth with the supply house over who screwed up but it doesn't matter because new windows are coming. It was likely a miscommunication or typo, not a mismeasure.
After initial feedback yesterday, I called him and talked through the remaining work, and I feel much better. He iss planning to caulk, insulate and cap but because the capping was delayed they're going to do all of that when they come back. They weren't going to leave insulation to get rained on (makes sense).
It looks like my primary concerns are relieved. Thanks for all of your help.
I do not get the impression that you have that type of relationship and am curious as to why?
I'm a young first time homeowner in a new town far away from my roots. I don't have a network of trusted contractors so I have to rely on recommendations from people I barely know. I'd be more trusting of someone that I or a family member had personal experience working with, but in this case I just met the guy. Plus, I like to get smart on things rather than rely on one person's advice. This forum has been wonderful in that regard.