Or we've also been exploring moving to a district with a better high school for the kids in a few years and turning the current place into a rental.

Is there a limit to how high I can go? 

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 ? 

Coupled with persistently high interest rates that may last for years, rising insurance premiums are inevitable, regardless of your property’s condition.

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.

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

The wrong property management approach will lead to the dreaded three:1) high drama,2) high turnover,3) high property damage.Use Household-led Property Management (HPM) developed and perfected for co-living.5.

While I do maintain a relatively modest percentage of my assets in money market instruments, corporate debt funds, and high dividend stocks, I remain most comfortable with the investments I specialize in and know best.  

Most of these folks don't want to lose their voucher.Additional issue, when rent is too high, it slows down leasing. 

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?