@Brandon Brown you have either done a boat load of research or have background in mechanicals! 

I plan on handling most of the cosmetic updates and mechanical repairs, to a point.

Life and long term care insurance are typically where you see this.After a lot of wrangling, the agent was able to get the policy renewed with the correct bank account number for the auto draft.  

Don't drive a new car to town; we have some of the best body and mechanics in Texas - in chop shops.Ah, just kidding. 

It's very affordable and will save you time with auto messaging, channel manager so you can list on Airbnb and VRBO, and some light task scheduling for cleaners and handymen.

I've been using State Auto for my Landlord policy which is due for renewal in January.

I just graduated from college in June with a degree in mechanical engineering, but I've found that my true passion and interest is in real estate.

I typically tell my landlords to have the tenant start with whomever does their auto insurance.

What happens when the repair company says it was an "auto-approve" repair and you say it was a "permission first" repair?

TL;DR:  You will likely need to pay taxes in both the U.S. and Canada, but the Canada-U.S. tax treaty provides mechanisms to avoid double taxation.