Just had our roof and siding redone after hail damage. We were told that the exterior insulation built into the siding was minimal and not worth the extra cost for the benefit. If you already have it and it just needs repaired that’s a different story.
From what we could tell, the main difference between exterior contractors was the brand of shingles and siding they use and how they structure their quotes. The job is pretty much the job other than if you choose to do different types of siding on different parts of the house.
We chose our contractor based on someone else we know that had good experience with them and them being local to us in case we had any issues or wanted to make a warranty claim (they offered a 5 year workmanship guarantee). Pretty much all roofing people also do siding. Most do windows too. Our guy did windows, roofing, siding, insulation and gutters despite only having “roof” in his business name.
Just get 3 quotes and see who you like. Also, if you are doing anything through an insurance company, DO NOT sign anything from an exterior contractor to let them negotiate with the insurance company on your behalf. If they came door to door, that’s often something they will ask for. Just assume that most of those door-to-door folks are in the same category as ambulance-chasing lawyers and don’t trust them at all.
Also, if you are going through insurance and the contractor wants to see your claim, remove all dollar amounts from the claim before you share it. Let them give a quote based on what they value the job at rather than based on how much money they know for a fact you have.
Also also, it’s illegal in a lot of jurisdictions, if not all, for a contractor to tell you that they will reimburse or refund the amount of an insurance deductible if you make a claim or if you choose them to do the work. So if any of them said that it’s immediately shady if not downright illegal.