Careful with the dens. Make sure you check out the room dimensions. Sometimes what people call a den is no more than a shallow indent in a wall that isn't even an enclosed room. Other times the room is enclosed but only large enough to barely fit a crib (not an actual bed) - more like a large closet. They are called dens for a reason (den = generally won't work as a bedroom).
Ah, good advice. So that's out as well. The more I dig, the more I think we'll have to stretch the budget close to 3K. What you recommend based on these points:
My workplace (when I have one) would be in downtown core.
My son's college (Humber or Ryerson) is closer to / in downtown.
Do we live in the suburbs, save on rent but spend more time commuting? (Don't plan to buy a car for 6-12 months)
Or live near downtown, pay more rent, save time?
I'm leaning towards living in and near Bloor/ High Park, as mentioned earlier. And looking at Ursula Franklin Academy and Humberside Collegiate schools for the daughter.