Update on Car Rental:
I went back to Paradise Rentals and as they were out of small 4 door sedans, we wound up with a Jeep Patriot for 5 weeks for $1500. As one never gets over 25-30 mph gas mileage is not an issue. The Partiot is a 4 dr jeep fully enclosed, which enables locking things up, as opposed to an open Jeep.

As to laid back bars, I offer the following:
Molly Malones - for Happy Hour in Red Hook ($5-6 cheeseburger w/fries), Elepant beer and others on HH prices.

Sunset Grill - Secret Harbor I believe, great tacos on HH prices.

Latitude 18 - near Red Hook, difficult to find the first time, open air across lagoon from RH marina area, what an secluded beach bar should be.

Off the Grid - Food truck on top of hill at entrance to Sapphire Beach area, great BBQ, fantastic sweet potatoes,beer, pop availabale - great view to St. J, not a beach bar, but definetely laid back, sit at tables along ridge overlooking islands.

Some other suggestions if you are going to be there for a while.

Groceries lower prices at Cost U Less, inland a bit between Charolette and Red Hook.

Cruzan rum was cheapest at of all places - Walgreens.

Strongest Pain Killers were on StJ at a small corner laid back bar - across the street from the Across The Street Bar.

Actually any of the beach bars on St.J along the beach down from ferry dock are laid back.

For an upscale atmosphere, and on the beach - Caneel Bay at the upscale resort on St.J was good with modest prices for lunch in cushy seating.

Thats a starter.