Hail damage roof and siding repair advice needed

We sustained roof and some siding damage in a recent hailstorm. I’ve had the insurance adjuster out and am waiting for his estimate. He indicated the whole roof would need replacement and that they may cover 2 sides of the house for siding (aluminum). I’ve also involved a local, reputable contractor who went over the entire house with the adjuster. The contractor says that for the cost of putting new aluminum on 2 sides of the house, he could do 3 sides in vinyl. That would leave an out-of-pocket expense of 1 side for us to cover the entire house in vinyl. The contractor is sending out his “siding guy” today to look things over.

I’m not too worried about the roof job as that seems to be pretty standard, but I’m a little nervous about switching from aluminum to vinyl siding. None of the exterior lights, hose bibs, receptacle boxes and vents have real mounting blocks- they’re all somehow attached and caulked (or not) to the siding. Our house was built in ’85 and is sheathed with Celotex Tuff-R so all of the nailing needs to be done on studs. Will the siding crew re-sheath small areas with wall penetrations with OSB to allow proper mounting block attachment? I assume all doors and windows that are caulked will now get J-channel. What other details should I be concerned with?

So that’s the situation. At this point, I’m hoping to hear from any of you that have been in a similar situation or have any words of advice to make this whole project go smoothly. Thanks in advance for your help!