However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

Especially now, I am seeing a lot of people who bought during or right after the COVID pandemic and are in situations where they simply cannot sell their homes for any profit (many of them bought as new construction).

Push through it, you may even need to have a second, consistent paying job and thats OK, until you get established.

That said, even with conservative rental income estimates, my living expenses would eventually drop to several hundred dollars less than what I’m currently paying in rent once the house hack starts generating income.I do have cash reserves to weather some rough patches, but the idea of pushing my budget this hard makes me uneasy.

If not, who do you believe the natural buyer is and why do you believe they will pay retail when they can replicate what you accomplished with any number of available properties on the market at any given time?

@Michael Daniel Ultimately, it's all about confirming what the housing authority pays.

We explained to him we would pay for probate and pay to fix up the house to get it rented.The lease is for 5 years but dissolves once we close.

In return, they will be motivated to get a job and pay back every dime owed while lavishing you with praise.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

Now, you need to figure out how to find deals and pay for them.