I have to agree with Chris that chartering is one of the best ways to gain experience with lots of different boats. We started bareboating 40' Navigators & Carvers, then discovered we rarely went faster than 8 knots. When we started looking at trawlers, we chartered a 38' Selene, then a 46' DeFever Trawler and became hooked. Every time we were out on the water, we looked at Kadey-Krogens, DeFevers, Selenes, Northwest Trawlers, etc., etc.
Have fun and try as many boats as you have time for!
Scott (Boydski) Boyd
Yes Please, Grand Banks Eastbay
Sea Eagle, Nordhavn 47 (sold)