Thank you all so much for the advice and support.

I would also want to vet their team (lawyers, CPA, lenders, PM, etc.) a strong supporting cast can compensate for a lack of direct experience.Do they have skin in the game?

Brain, we can tell you don't have good support here. 1) Transferring/Contributing to the LLC is a non-taxable transition.

All other consumables (utilties, etc) will be paid by the tenant.

I also make enough to support a 3k+ mortgage a month if needed.Does anyone have any suggestions on how I could leverage better or should I start with (1) then move up from there?

Unfortunately, Appfolio's customer support and training has been less than Satisfactory.

The difference is we had boots on the ground support & paid them.

@Bishara MubarakYes a 203k should work as long as your credit and income support both mortgages. 

Let's be honest: most of these stuff are needed in every household and I am pretty sure that some of my cleaners occasionally used some items purchased for the properties (I used to have a 3be/2ba house to consume 12 rolls of paper towels within 5 days).

I would let them know by law you can't say no to an ESA however your policy would generally consider that a single person would need a single support animal.