Cabarete is the place for wind in DR. Summer is the best time, but now should not be bad either. I was there last year from Feb 10 through Mar 10 and got 25 kiting days out of 30.
My advise is not to go all inclusive.
Check out places like Millennium, Ultravioleta. All brand new, ultralux hotel/condos. There are plenty of dining options 5-10min away, and also decent nightlife.. Not as crowded as Wydham and much more exclusive. Needless to say, you can rig your kite just 50ft away from your room
There is also Seawinds, Watermark and many less fancy but good places, to fit any budget.