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 ? 

This is a straightforward process that we’ve followed to consistently deliver high-performance properties, and it does not require secrets or gurus.

I am a general contractor that specializes in kitchen remodels and high end custom cabinetry, but I'd like to use this project to pivot into more general contracting and property development. 

Talk to your attorney, and if you dont have one, get one - as @Ken M. said, this is highly specific to the state and the circumstances.

I highly recommend consulting with a CPA or tax professional to ensure you're using the best strategy for your situation.Good luck!

It can eat into your cash flow, but if you're earning high income from your W-2 job (I assume you are if you're buying in all cash), it makes more sense to use your time making more income versus managing maintenance requests as you scale. 

These are things at the high level I want to be looking at for all my real estate purchases. 

Nobody wants to be around people like this, so I’ve had to lower my rent drastically and have a high turnover rate here.

If you are using it to buy a turnkey property which needs to produce cash flow to be considered a viable deal how does buying turnkey(Little to no cash flow) combined with HML(High interest only debt) make alot of sense financially? 

@Eric L ConryThis is a highly personal choice.