I agree that it depends, but I've gotten over that and now I always select a window seat on the right when facing front (on the planes I tend to fly on, it's seat "F") for the arrival and the opposite for the departure (seat "A").
When in seat "F", you have lots of options for what you can see, usually more than seat "A" though on any one flight "A" could luck out and get a better view on that day. Most of my flights head to the DR out of Toronto, so not all that far from Detroit. We head to the ocean and then south. I have passed over Cape Hatteras but we don't usually stay over land any further south than that. …webshots.com/photo/2225531330064234328umvqiS
Once at the DR, I've passed to the east of the coast and seen the Dominican beachy coastline on my approach (…webshots.com/photo/2043488680064234328hRnGTh), on another flight we cut across Samana (a half dozen pics of that area at http://travel.webshots.com/photo/2167696830064234328ZqJkkL) before heading inland when we flew over Higuey. It was very cool to be able to see the basilica from the air (…webshots.com/photo/2758932830064234328Patqad) before heading to the coast (…webshots.com/photo/2554717660064234328vdXNpY)
I've flown over the islands north of the DR as well and look forward to it, but for my recent trip we were avoiding a weather system in that area and went out of our way further to the east having us land 15 minutes late and missing a lot of good views. If made to choose, I'd rather a smooth flight so I was okay with the decision!
Though you can see something out the left, I've never seen anything better than that which I've seen while sitting on the right.
Kaki