You are correct, @Mike Franco in that the C.A.R. lease agreement language states that neither party has any obligation to renew and expiration of the lease, tenancy is terminated.

As far as being the middleman for a transaction and the property never officially being in your name you can get in a lot of trouble for that up here without a license.

My company became official and legal in fall 2017.

This sounds like a language issue to me. 

Why cant it just be "get a loan from a private lender, flip the house and sell it out" or "get a loan from a private lender, flip the house, get an official loan from the bank (Refinance) and sell it"?

He will be moving in with girlfriend on this date; however, she will be moving into the new place in Madison starting June 1 (i.e. two months prior to him officially moving).

This is a particularly surprising remark coming from an attorney as we're both in a business where language matters... 

There's no better tuition than going through all the motions- coordinating with lenders and contractors, learning how to gut a bathroom and rip up carpet, having to deal with house inspections and code officials etc. 

New leases can contain language for a fee that you'd charge monthly and they would pay the utility remainder on top of that.

All the city officials that I have dealt with in College Park have been very professional and helpful, it's like a small town there.