This is key - Duing the entirety of your reverse exchange process you are actually double dipping revenue flows and appreciation.  

I keep the properties in the company name with me as the only stock holder and officer, and my personal assets in tenants by the entireties with my wife so they are completely protected. 

I don't know the law in FLA on this point, but in IL a PERSON can always represent themselves (but remember "He who represents himself has a fool for a lawyer"), but a legal entirety (such as a HOA) must retain an attorney for court/pleadings. 

Between my roommate and my tenants, the entirety of the mortgage is paid, and I have a small cash surplus each month after minor expenses, so the entirety of my earned income can go straight into reserves for the purchase of my next property.What matters much more to me, as far as my house-hacking business is concerned, is my cash cushion, which you lightly touch on.  

Otherwise this thread in its entirety wouldn't even exist.Further, the premise that simply learning something, somewhere is better than not doesn't hold to be true.  

In either case, the entirety of the Scope of Work is identical whether contained in a single or multiple "contracts".

I am thinking of of using the entirety of my 403K (it is the teacher's equivalent to a 401K, sort of) and about 3,000 of my 10,000 emergency fund savings to pay for it.

ASSIGNEE ACCEPTS ALL TERMS AND CONDITIONS OF THE CONTRACT FOR SALE AND PURCHASE BETWEEN BUYER AND SELLER IN ITS ENTIRETY.3.

Consider this like a probationary lease or even a testing lease.After that 2 months, if I was happy with his tenancy, I would instate a 1 year lease.I also immediately raised rents on him but not the entirety up to market prices yet.

Generally speaking, a tenant is liable for the entirety of the lease term unless the lease allows for early termination and those allowances are satisfied.