This conversation popped up today between a friend and me. Her entire sailing experience is 2 years as rail meat crew on deeper water racing boats. I've done hardly any racing, but have many years of practical experience on a Sunfish, a Boston Whaler Harpoon(~16 ft), a Hunter 23, and I'm about to embark on my life's Catalina 28 phase. When I mentioned to her that I'm in the process of selling my 23 and asked if she knew anyone who might be interested, she responded by saying that none of her friends sail "small" boats. I laughed because from my experience, 23 is still big. My Sunfish experiences are still my frame of reference - without which I don't think I'd ever have established my "feel" for wind and current shifts - and how to properly respond to them. From my perspective, without that experience I might never be as sensitive to conditions in boats with bigger LWL, and couldn't possibly sail them as well. Clearly it's subjective. What's small to you? What's big to you?