Here it goes. I currently own an O'day 22, and have sailed the heck out of it over the last 2 years. My wife and I stay overnight on it almost every weekend during the summer. We are thinking of moving up in terms of boat size. I don't have an extra 10 grand sitting around, but we dont own a car so a loan won't be a huge deal. Here's where I need some advise. I think we should move up to a 27 or 28 footer that we'll be more willing to put some money into and keep for 5 or 10 years instead of buying a 25 or 26 footer that we'll (or I'll) tire of quickly. What are your thoughts? I am in love with Islander 28s but they a few and far between for under 15K. What do you recommend in terms of boat progression? I want something that can hold its own and keep us comfortable in a stiff breeze. The shoal keeled 22 footer isn't a treat in 20 knots as you can imagine. In short, do I skip the 25 range and go up to something a little short of 30? Any recommendations? Anything I should avoid? I've accepted the fact that I will be throwing money into a hole for as long as this sailing fever grips me, so should I throw it into a hole thats next to a bigger hull?AdiosAndrew