What does this group recommend for a single tenant CRE (occupied since 1983 - not sure if by same medical facility/need to confirm )- that is a medical facility 2 years left on the lease. numbers look good, but I want to get thoughts on if a single tenant CRE is riskier than going for a strip mall with multiple tenants

so even if you do find someone that will lend in  junior position or cross collateralize, they may not be willing to do that against an owner occupied property. 

Assuming you're going to occupy the new property as you stated, you might qualify for low DP programs, which I believe have limits to the loan size (which one of the lenders here can probably tell us about).  

You can't try to owner occupy and evict them.

Also a new occupier or owner would conduct something call a phase 1 or phase 2(environmental site assessment).

Are you planning to occupy part of all of the rental? 

Hard Money/Private Money can provide up to 75/80% LTV on Refinances at rates starting at 7% with a great FICO and can close in 2 weeks low doc and no do options for Owner Occupied investment properties

One month the landlord could be 100% occupied and the next 60%.

It is currently tenant occupied - they are good tenants but have a low rent. 

If you owner-occupy you can finance it FHA or VA, come in with little money down, and you can skirt some of the STVR regulations in Savannah (as long as you purchase between MLK and Broad and north of 37th-ish (I forget where the exact line is.))