Myself also being a Puget Sound guy, I have a few opinions on the matter. My parents and I have a beach cabin on the south end of Whidbey Island. Of which I've got a 2004 GW 228 Seafarer and she does just fine in the 1'-2' chop. I've thought about "upgrading" to a slightly larger boat like a 232 Gulfstream, but the majority of what I do is trolling for salmon, checking crab pots and so forth. I've got a mooring buoy out in front of our beach cabin, to where most of the time I'll paddle out in my kayak or dinghy, climb in, start up the boat, unhook the boat from the buoy, hook up the kayak to the buoy and then literally start trolling for salmon from there. I do cruise in the boat, though it's usually weather/wind permitting, kind of like everything else. Last weekend we were up at the cabin and the winds were at gusts close to 30 mph, and even if the fishing was open, I wouldn't be out there in those conditions especially by myself because it just wouldn't be a lot of fun. I realize that most people don't do the kind of fishing/boating that we do out here in the Puget Sound and that most don't likely have a mooring buoy.
That being said, there are dozens of boat ramps in the area to where even if the weather/wind was quite bad and you still wanted to go out fishing/cruising, there's likely a ramp that's quite close by to where you could launch the boat there instead of motoring the entire way. My neighbor has a 2005 GW 270 Islander, of which it is imo just too big, and I think he would say the same thing as he's selling the boat and going with something smaller/different. I think you need to ask yourself what your primary goals are with the boat, what you're going to use it for the majority of the time, etc? With the Puget Sound being quite well protected, we don't usually get a ton of bad weather, although we do get random days here and there like we did last Saturday. But as mentioned with my neighbor's boat, I'm thinking anything above the 232 Gulfstream would likely be a bit overkill out here. And as others have mentioned, even 30'+ boats are going to have their limitations to them. I'm of the opinion that if you're out in a 30'+ boat and are getting the snot kicked out of you, why are you out in the first place? That doesn't sound like it's going to be much fun. The same goes for a 232 Gulfstream in that some days are better for just staying ashore and not going out, as the elements aren't going to make the experience very fun. I'd give the 232 Gulfstream another try and see if it's like what you alluded to, to where if it was actually the boat giving you issues, or yourself just not being very familiar with the boat.
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