You could wholesale for say $5k, or you could create and endless stream of cash (in excess of $5k).Something to think about,Luke

Since you state that the homeowners were in some stage of the repossession process a knowledgeable attorney may have ammunition, in addition to your lease option agreements, to seek remedy in court. 

I am looking for some advice in regards to the best contracts to use for every stage of the wholesale transaction in MA as well as the most transparent verb-age for clear disclosure; and also the best clauses to use to cover oneself risk and inspection wise that would still be presenting the seller with the most attractive offer possible.

At your stage the lawyer will be more involved initially in determining business structure.

I am at the beginning stages of getting into multiunit properties in SWFL.

For now I am in the accumulation stage but I'm being very careful with my next steps especially in this market.

How about staging the outdoor/patio area with inexpensive indoor furniture from Ikea and spraying then, so, that they'll repel water? 

Probably your tax assessor will get involved in the later stages. 

Because if you utilize YOUR Lender, all the risk from then on is being taken by YOU until your gym buddy makes good on his supposed ability to do a "proper" Loan at some stage (as far as I know)!...

I would request to see the prior 3 utility bills.If these bills average $300 then yes I would pay the $600 to cover the excess.