Sorry if I sound a little Complicated.

I have not asked about how this would complicate taxes and whether or not an LLC would make things easier or more complicated come tax time.

Also hoping to do other small work through my company,such as lawn mowing,snow removal,painting etc. to make some extra money to put towards investments.Myself and my Canadian girlfriend are currently in the process of her sponsoring me to get my Canadian permanent residency,which has been a long,very complicated process!

Brent, this can be complicated. 

I've read many times that it's a complicated transactions with certain risks if done improperly.I do understand the risk of the due on sell clause.

Enforcement of the lease, rules and regs is more complicated.

Ify, don't over complicate wholesaling.

Since you cannot borrow or loan money, that does complicate some things.

Navigating these processes, providing all the paperwork and getting all the endorsements was a complicated and time consuming process.  

While your family's situation has similarities to the original post, the fact pattern is dramatically complicated by the need to address probate laws in your grandmother's state.