I didn't mean that this isn't a job for a roofer either, hvac just popped into my head because the v in hvac stands for ventilation. While working with hvac companies I have installed many attic fans and would never do something as dumb as that.
If an hvac company doesn't know how to cleanly remove shingles with a flat bar and slide flashing under the shingles to where the shingles cover the flashing past the actual hole in the roof, they have no reason to be in business.
Seeing that you know about the humidistat trick is something that I would think most roofers would overlook.