Slowly increase her rent over the years which defeats our purpose of house hacking or bump it up to market value and put the ball in her court to see if she still wants to stay?

State late stipulates that if it is exactly on property line the neighbor gets a say, and can also be billed for a portion of it, and taken to court if not paid. 

I am currently in the process of looking into buying my first rental property, however, I live in Toronto and the properties I am looking at are in Windsor due to my price point.

When I called the court, I was told that they regularly occur at the courthouse steps, but the lady in the phone was unable to tell me when the next one is.

Right now in Windsor ON where I invest, it is difficult to find properties that meet that standard.

If (which it won’t) and up in court, you can easily say that ‘hey, he owes $$$) per the letter.

Yes I spent a few hours and I have to make a few trips to the city dump(Doesn't cost anything and its a 2 minute drive) but the tenant is difficult and I wouldn't be surprised if he made a big deal about it and wanted to take me to court over it. 

Can the tenant request their entire deposit back and force me to pursue action through small claims court?

Go to court and file for eviction. 

Will the city of Cleveland provide lists via the courts for homes which have had water lines shut off?