I don't know loads about that sound, but we day sailed it (my brother and I) years ago in his 17 foot Newport. I'd suspect the best boat in that range would be the one with the least draft. One thing that struck me the most about the sound was how incredibly shallow it was in most places. I'd probably put centerboard boats higher on the list than fixed keel boats, mostly because if you run aground then, at least you'd be able to lift the centerboard and sail off. Off the top of my head, ODay 26, Lancer 28, Beneteau 26 (the Euro model with the swinger), swing keel Catalina 25, you see where I am going with this. Second on my list would be wing keel models, mostly because if you run them aground they'll be harder to get off the bar than a swing, or centerboard. Shoal keels or full keels might be a consideration.