As a Realtor in the area, let me give you my thoughts on this.
When looking at purchasing a home, you shouldn't focus solely on "bang for your buck". You have to keep in mind resale value and appreciation.
The reason real estate is so expensive in the GTA is because of soaring demand for pretty much anything type of property. May it be condos, townhouse, semis... Your resale value is going to be very good, and even in tough times, will remain resilient and bounce back quickly. However you're going to have to make so many concessions with that budget. Won't get you that far in the GTA.
That being said, there is a huge advantage buying property in Windsor, and is what many Realtors are doing now as part of their investment strategy. Windsor is set to be one of the fastest growing cities in Ontario from an economical standpoint. Demand is increasing at a fast pace, and I myself am in the process of buying a 2 bedroom house there.
Remember, when thinking of real estate, think mid/long term, and don't think of it as your forever home. The average homeowner in Canada changes home 2-3 times in their lifetime. With the way real estate is growing here, you should focus on getting a foot in the door not too far down the road.
Strategy of buying a home in Windsor to me is a very sane one, provided you have your ducks in a row from a professional standpoint. I mean you don't have any commute to/from GTA.
Here's what the future may look like:
-You buy a 2-3 bedroom house for $400,000 today. 5% down. $380,000 mortgage
-$2300 monthly payment
-In 5 years could be worth $600,000
-When the mortgage comes for renewal, sell for $600,000, pay off the initial remaining loan amount of approx $300,000
-Pocket the $300,000 equity and use it as downpayment to purchase a new home.
-Get the new rate which we all foresee to be much lower than now.
-Either reduce your monthly payment by sticking to the same purchase price
-Or keep the monthly payment the same by upgrading
Lots of possibilities. Shoot me a DM for a few tips.