(Many people just assume it'll be fully tax-free because they lived in it somewhere)

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 ? 

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.

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

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

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

Generally larger commercial properties and shopping centers are easier to classify with hard and fast rules, but to the points above the residential areas really move very quickly and have way more nuance than most people care to admit.zip codes are generally way too large for my liking at least in my market to provide any kind of insights other than macro level economics but even then highways or rivers that cut through a zip code can end up with totally different trade areas.we can get pretty granular with cellphone data and with grocery center data to understand the trade areas and their true boundaries, but that kind of data pull is generally only cost effective for investors doing larger scale projects or developments, and honestly we still just end up getting on the ground and feeling it out, so I generally tell people that the money is better spent on a plane ticket and weekend trip in the area you are looking rather than any kind of "trade area" level data studies.and generally B class in 1 area means something different than another. 

We are the kind of people who do not jump into anything without fully planning it out.

Also, do you have 2 people per room, or just one person? 

So, many people in your area may not realize its negotiable and just assume its always handled a certain way.