When that portion was complete, I could then receive draw money which allowed me to pay my utilities, taxes, and mortgages.

• How do leases typically handle furniture/appliance damage or wear?

You typically need up to two years of stable employment before a bank will loan to you.

Utilizing empty lot space in this way helps to combat the increasing housing prices and limited supply many markets have been experiencing.

You need to work with a lender that will utilize STR 1007 Data and/or AirDNA Income on a REFI.Tough deal but we do this consistently.

I plan to utilize some cash, margin loan, 401k loan, and a HELOC as a down payment.My first house hack (now an out of state investment) has a Zestimate of $530K, and I have $266K left on the loan.

My thinking is that by renting to a residential care facility I can effectively utilize all the space, earn above market rent, and help provide a needed service, while avoiding tenant parking jams. 

This is limiting my options.I have never utilized the multifamily lending products offered by Fannie, Freddie, etc., so I would be interested to a) hear other BP members' lender recommendations for this sized property and also b) other members' experiences working with Fannie, Freddie, etc.  

Which size of home is typically perform best on a cost benefit analysis?

You'll have access to owner occupied loan products, therefore saving on your down payment, typically 3-5% compared to 20-25% for non owner occupied properties.