I am assuming insurance, taxes and some local fees would be applicable as part of the expenses. 

And just for your own calculations it's safe to estimate mortgage rates a little higher than standard rates.

Actually buying in a place I lived before moving to CA, it has had very strong long term growth for many years and I already have all the necessary infrastructure in place (agent/mgr, insurance guy, etc.)

 $66k left on the loan ($600 month payment with taxes & insurance).  

However our standard GRAR contract states that the buyer has to list (with appropriate inspection reports) the items they want fixed.

Taxes and insurance will eat over half of that. 

I've been told that umbrella insurance might be a better option, simpler, cheaper, while providing adequate coverage for most individual situations.Any thoughts? 

., pay for property insurance, rehab cost, etc. with your personal money)- Using non-recourse loan: As Jason suggests, you can take out non-recourse loans for your IRA/401k investments.

We sound like the start of a bad joke:  A retired attorney, and two Property Insurance guys walk into a bar... 

.- I would get a lender's title insurance policy to make sure you are indeed in first position and the person/entity you are lending to is the owner.- Borrower pays all closing costs, usually subtracted from loan proceeds upfront.- Make sure the interest plus points doesn't exceed usury in your state, I don't know what it is in Florida.