I haven't read the whole thread yet, but I moved from a small town to Toronto in 2014 and had considered buying, but after seeing the crazy sticker shock for myself, I opted to just rent.
I'm sorry I don't have good or promising news for you:
For anywhere that is a 45 minutes commute to Toronto's downtown financial district you will expect to pay:
$400,000 CAD minimum for a tiny 1-bedroom condo,
-OR-
$800,000 CAD minimum for a house that is >100 years old and literally falling apart.
After seeing a few friends buy houses in the city (including friends who bought in Leslieville and the Beaches areas that were mentioned above), each of them have had to deal things like:
-collapsing roofs
-disintegrating foundation
-asbestos / lead pipes
-termite damage
-one friend literally fell through the floor as the wood planks gave way from being so old
Each of them have then had to deal with years of extreme renovations, basically completely gutting the inside of the house, having to go several months unable to live in their places while renos are happening, and hundreds of thousands of dollars in unexpected costs above what they had already payed. It has put huge tolls on their marriages, and they all regret buying their houses. Having seen what they've had to go through, I am exceptionally glad that I gave up on the notion of buying real estate here.
So you can expect to have to pay at least $1 million-$1.2 million CAD for a house that is in even remotely decent condition, unless you REALLY love doing a lot of home renovations.
or $500,000 for a decently sized 1-bedroom condo.