I would definitely choose the Simpson Bay area for being closest to several casinos and plenty of restaurants serving the type of food you suggest you enjoy. I too enjoy the casinos in the evening and there is lots of nightlife in the Simpson Bay area.......bars, movie theatre , clubs, casinos etc... A lot of these things can be walked to as well which makes it nice. I have stayed in both Maho and Simpson Bay and would still choose the Simpson Bay area for sure. Also the Maho area has not completely recovered yet from Hurricane Irma so it is still a bit desolate there. Whatever you choose, enjoy your trip and definitely choose St. Maarten over Aruba. You will not be disappointed!