If it were ME, I'd choose Simpson Bay Resort. You are in the heart of Simpson Bay, with tons of great restaurants close by, a decent beach there at SBR, but close to Mullet Bay Beach and Simpson Bay Beach. All of the units at SBR have been renovated within the past couple of years. Not sure about OBBR. I know some of the units there are renovated, but I don't think all have been. I am not partial to Oyster Bay, because there is not much right there in Oyster Pond that I am that interested in, and while there are a few restaurants there, there are many more, close to SBR, as well as casinos and nightlife. I am not fond of driving that road to OBBR at night, as there are large ditches by the side of the road. OBBR is closer to Orient than SBR though.