Re: Any good roofing experts?
Sounds like it's going to be a more involved project than just roofing. If you can see daylight, the roof has been in a failed condition for a long time and there could be structural damage.
I'd recommend finding a reputable general contractor who can manage this, as it will likely involve framing, insulation, and drywall in addition to the roofing. One advantage of a GC is that you write one check and they pay the subcontractors; if you have to get a loan for the rehab the lender may require you to use a GC.
I don't know how things are in Ontario, but in many U.S. states many of the specialty contractors have general contractors licenses, but it doesn't mean that they have the experience to manage an entire project. It means that they've passed certain tests and paid fees to qualify for a GC license which lets them hire subcontractors and get different insurance.
The "Senior Member" designation under my name doesn't mean I know a lot, it just means I talk a lot.I've been a DIYer since I was 12 (thanks, Dad!). I have read several books on various home improvement topics. I do not have any current code books I can refer to. I was an apprentice plumber for two years.