I see benefits but I'm trying to understand the full context of building this from ground up.

If they can't control there spending (or pay them self first) it's unlikely they will find success as a REI.

I would be curious to see how this plays out in the end.Exactly, more than likely both are at fault by not paying attention or caring.

They would pay all utilities and maintenance on the property and provide 2 months security deposit. 

But, when there is an emergency you are sure glad that you have been paying all of those years.

I am looking to vacate the house and prep for a 1031.I previously had the property listed, got under contract just for this tenant to be the reason we didnt make it through the inspection period.I have a good relationship with her but she is a mess, pays late every month (including her late fee, she is current), police visits, etc. 

You also have to consider your holding costs - you are paying HOA fees, insurance, and property taxes.

It's difficult - often impossible - to verify their identity, address history, ability to pay debts, or criminal history without a social security number.

However, being a Canadian citizen, it seems like I would still need to pay Canadian taxes on the US properties regardless. 

The teachings free, you have to pay for airfare and hotel, I'm assuming.