I fear that if I go to apply, and do things the right way, then the city will deny me and I will be under their radar.

Sounds like you are thinking about things correctly and don’t fear good debt that produces cash flow.

Fear might hold you back. 

@Dan Heuschele Your right, landlords are not required to accept emotional support animals, however most landlords seem to be in so much fear of the Fair Housing Act that they throw logic out the window.

The one thing that nags me in there and would need some legal fleshing out is how close that is to a step transaction. 

If you show your wife the increase in income by buying more, then maybe you can alleviate her fear of holding more debt.These are business assets, it's best to treat them as such.

The only way to do that legally on a regular basis without fear of legal issues is to become a licensed agent.

My only fear for doing something like that is the timing for recording prior to the trustee sale. 

Nothing exciting here but one of my fears is that a quest's dog will get sprayed by a skunk at our VR in the country and it will get in the house, ruining the carpet & furniture, lol.

Offer to pay for his entity creation and a review of his taxes by an accountant instead of Turbo Tax that he must be using, because I'm unaware of any scenario where it makes sense to avoid making money due to fear of taxes - in exchange for granting you the lease option and covering those expenses could be your option fee.Rral Estate is a tax shelter...