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 ? 

Investment Info:Small multi-family (2-4 units) buy & hold investment in Piffard.

Or only buy something for $350K and pay tax ont he $100K difference.

You can take out a lot of complexity when you buy property that only needs maye paint & carpet.

I'm interested in flipping, and short-term rentals at the moment to build good cash flow, then pivot into more of a buy-and-hold/appreciation play 10-15 years from now.

I’m currently house hacking and planning to buy my next property in about 6 months.

We all invest in real estate in order to make money, and keep in mind that someone who can only afford to live in a mobile home and seller-finance to buy the land is probably tight on funds. 

I considering buying my first rental property there, and am an out of state investor.

One of my goals for this year is to buy a property OOS and another one in my backyard.

Quote from @Roxanne Whitaker: Please be aware if you buy an investment property and do not live in MD, when you go to sell it you will pay an 8% tax at settlement.