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 ? 

It's a great way to talk through your plans and goals for real estate with people that actually understand! 

I want to hear some stories on how other people got started and how easy/difficult it was.

I'm certain there are plenty of people in the community willing to help. 

The problem is mainly a concern for people with a net worth or reasonable income. 

My immediate area, 5200 people, has 3 outdoor self storage and 1 new climate controlled.

I personally don't mind cooking on electric but I will say that cooking on propane is different than what most people know which is natural gas.

Early in my investing career I wanted to cost seg my properties, but my accountant told me I was wasting my time because I was unable to use the full depreciation benefits I already had.  

I bought a single family because I thought I could house hack in the same way as a duplex and in ways it certainly could have and did work but I didn't expect the relational aspects of having people living in a property I purchased.

., Buy early December, on your own or with your spouse be the only housekeeping staff and maintenance people, rent one or two weekends, voila...