Matt, I fish the same waters from May into November. I fish a 2510 dv w/ twins. I can not comment on the lesser degree deadrise Parkers as I have never ridden on one. I have "captained" the boat for about 500 hours and this past season I seem to have finally figured out the ride. I also have fished on a 23 Tender, 22 Mako, 33 Hydra, 24 Cobia, 25 Luhrs, none were as stable as the dv Parker. I do not feel any lack of stablity with this boat. She fishes at anchor well and drifts stern to. There are few days that I do not leave the dock because of poor weather.
Honestly, during heavy wind, I'm more concerned about getting back into the slip than the ride ( the bow is difficult to control in this boat and I have yet to figure this out ). I think the permatrims installed help this boat tremendously. Fishing from the Vineyard to the Block you will encounter nasty conditions. Buzzards will kick in the afternoon, the mouths of the Sakonnet and Narraganset can also develop confused chop. If in fact some of the fellow Parkerites have ridden in both models in the same conditions and can say that the dv is a better ride, I would opt for the dv irregardless of the distance you'll be traveling to fish.