Owned a 27 CC Grady that was 8'6" wide for 8 years. Moved up to the 271 two years ago and best move I ever made. Wife and grand kids love the big seat in front of the console but what I love is the bigger beam. Dealer told me it'd be much better ride but I thought it was sales blah blah blah. It's a Night and day difference in back bay chop and the ocean when I run offshore. Problem I see is 9 and 1/2 is a lot to trailer. I have slip in NC so only haul once a year. Don't know about the 28 footer I thought 271 replaced it. Both same width so ride should be just as good.
I moved up to a 283 Release CC last year (2005 model). I love this boat! Wide beam, runs great in the ocean. Like any other CC with the wind in the right direction you will get spray. I am a firm believer that bigger is better.