Thanks highops!
I just randomly booked Lahaina grill, so changing it to Fleetwood's isn't a big deal if its recommended, I'll also check out Gannon's. Out res at Monkeypod is currently 6:45 - maybe I'll make it 6pm and head over earlier for Happy Hour, or maybe we'll head to the later HH after eating elsewhere.
I'd imagine we can rent/use chairs & umbrellas at the beach south of the Marriott - I'm considering picking up some cheap items from Target (or similar) just to use during the trip.
I got a car for $240 all in for 1 week through AutoSlash and will continue to monitor.
Good to know about the beach just north of the Marriott (which seems to be closer too).