(Even if your form has a space to list one, it’s not something that’s legally required.)It sounds like you’d also like to increase rent.

If he was living there with previous tenant’s permission, then he’s not a squatter and he had/has a legal right to live there.

I'm not sure if it is legal for him to list his "contract" on the mls, but he does not need a license to sell his contract.

Can you legally purchase the property for back taxes before it goes to auction and then rent the property to those who are still living thier?

There are websites selling ESA "certificates" and vests that are not prescribed by a doctor and legally not acceptable, BUT there are now websites with doctors selling ESA "certificates" and they are probably legally legitimate. 

From a tax perspective there's no advantage.I'm not an attorney, so I can't speak to the legal side.I think the K.I.S.S. ideology goes a long way with beginner rental property entity structuring.For example: if I was just starting out and buying properties in the Indianapolis metro, I'd form an Indiana LLC to buy up the properties and call it a day. 

I want to be legally straight.

And guess what, he was given a cease and desist order, shutting down his business until he had a new location where he could legal run the business. 

I'm a broker, not an attorney, so seek professional legal advice.

Preferred is 2 seperate leases, just not entirely sure if this is legal.