So even if you pick a state with stronger protections like WY or NV, the cause of action arose in the state where the tenant fell, so likely that the court where the accident happened would have jurisdiction.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

PA doesn't even limit late fees by statue, but I suspect there are court cases on excessive fees that have set a precedent.

The owner filed notice to quit, I believe a 30 day no fault, and has entered the complaint with the court as of 9/16. 

Most of the court documents are above my pay grade, but it does appear his eligible debts (which appears to be most of them) were discharged, except for re-affirming a car loan.How do I determine if that bankruptcy presents a problem as an investor?

I am curious why they would not be able to reference each other though. 1 year should be the max you sign for both of the agreements...lease, and Option.The reasons you keep the contracts separate are many starting with:1 - You limit your options for selling the Option Agreement2 - You handcuff yourself to the Owner of the Option for too long a period, mainly because...3 - Most Options, in a LO arrangement, are rarely exercised after 1 year.4 - ...and the big one, you will be one court case away from having your agreement turned into a Land Contract 

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.