In all it was 12K for a new roof with Owens Corning Duration shingles including tax.Thanks in advance!

The CCR's likely have language with the allowed duration for "guests".  

duration of contracts for these traveling staff?

This means that an owner cannot legally operate a short-term (less than 30 days) vacation rental in the county, except for one zoned residential, multiple-family on the barrier islands.City of SarasotaThe city of Sarasota does permit short-term vacation rentals with a minimum lease duration of one week.

They did not require earnest money and all rehab was on there dime so I did not have cash tied up in the deal for that duration. 

Which ever formula you decide on, it’s the one that you should stick to you for the duration of the tenancy. 

Duration of the loanCan I make all payments at the end?

You guess correctly, you should be able to apply for a HELOC,    The duration will vary from institution to institution. 

I don't think the upper upper midle class will spend $400/night for B+, they'll shop the market to see the A+ for $500/night and make that the destination and for less duration.

If the lease is below market, or for an abnormally long duration (subject to interpretation) it CAN be invalidated.