Such a complicated approach to a relatively easy situation.Definitely think that paying off the mortgage is pointless if he's just getting another.

This is not complicated folks, what happens as affordability to OWN your home decreases?

Honestly, you should have just stopped at Facebook.There’s nothing quite like receiving an unsolicited online message, random proof of funds, complicated background story, sketchy work locations, and a foreign accent to scream scam any more loudly.

I understand this is a complicated process, but I’m excited for the challenge.

If you are the LL, either an attorney can write one up pretty quickly if it's a complicated lease with special provisions, or your State Association of REALTORS should have a promulgated form you can use (I've had people pay me $150 to write on up for them in Texas where I'm licensed). 

Note: A more complicated way would be to also setup a business account under the LLC, and have my property manager distribute the funds to that business account.

It needs to be as simple and efficient as possible.Some of our Clients get caught up in having these super complicated (fancy) entity structures for maximum protection.

It’s a great situation, but rather complicated and hoping for some guidance. 

Some items can go either way depending on tax strategy to further complicate things.Thanks for laying this out, @Michael Plaks.

If the free rent were considered a gift or was taxable that could be a complication.2.