MA roofing contractor recommendations – GreenBuildingAdvisor

The roof on our 1961 ranch (standard gable with asphalt shingles and plywood sheathing) in Climate Zone 5A is coming up on end-of-life soon and that would be the time to install insulation board on top during the rip+replace. Looking for recommendations for roofing contractors that would be up to the challenge of this non-standard install.

Would I need to involve a second framing/carpentry contractor afterwards to deal with any added trim due to the built-up roof thickness?

Wondering how people are managing this if this is the way they want to go and avoid losing the opportunity.