If you are buying in Toronto I would be pleased to talk with you privately. Many of your issues are self answerable see the reply in the other forum you posted in.
I am very positve about Barrie I sold one there for 259,000 detached 4 years old nice house tenant at 1500 per month, the numbers work.
Maybe an older condo 275,000 will get you 1600 square foot 3 bedroom in a great building near square one. Rent is almost 1800 per month.
David
647 218 2414