We ended up going with
Canadian Roofing Company.
They had a good quote, fully explained the process and work involved, and overall quite thorough and friendly. Better than all the other sales people that came out. He's also an East York'er (where I live), so at least I'm supporting a family-run local business too.
Thankfully the roofing portion isn't contracted out, he has his own employees. Only part that is contracted is the aluminum work which is understandable. He said he's been using the same guy for years though without any issues.
Total price is a bit under $9000 after taxes. That's stripping the roof, replacing any rotted boards (100ft included), removing the chimney, 6ft of ice/water shield (everyone else was only doing 3ft), synthetic paper on remaining portion, adding 7 vents, IKO Cambridge shingles, refacing the front gable with vinyl siding, and all new fascia/evaestroughs.
Thankfully, he takes all major credit cards too, something most companies seem to avoid doing, so that adds a bit of protection should something go wrong. Definitely not comfortable giving people $9k in cash/cheque. Also, no deposit needed either, so really, it should be worry free.
I'll post some pictures once it's all said and done. He hopes to do it within the next 2 weeks, but obviously it depends on the weather.