I dropped by my local GW showroom today where they had a 235, 255, and 285 on the floor. Single 300 on the 235, dual 200's on the 255, and dual 300s on the 285. The price difference in the new 235 and the 285 would be over +$200K. It's $100K more than I paid for my well equipped 275 so I'm pretty happy with my choice as well. I'm like you, a real upgrade for me would be the 307 or 325 but I just didn't want that much boat for my casual day use with just a few people on board.
If I were to really change my boating goals I think I would be looking at one of the swift trawlers in the 44-48' range to open up real cruising experiences. A friend has been using his Beneteau 44 Swift Trawler for a couple of years and really loves it.