Tradin up: Your sailing objective
I have wrestled with this decision many, many times. To find out if I liked bigger boats (i.e. 30feet and up), I joined a sailing club for 3 years and sailed boats from 28 to 42 feet. I even tried multi-hulls.Bottom line: You have to identify your sailing objectives. Are you a day sailer, coastal cruiser, or blue water sailer? Bigger boats take more time, more money, more people to crew, bigger slips/moorings, but offer greater cruising comfort, more speed and ability to handle heavier weather. A second consideration is the wife/family. If she/they love sailing, you've got it made. If not, stay small (to avoid the inevitable 'sailing widow" lament)In my opinion bigger boats feel more like "yachting", whereas smaller boats feel to me more like "sailing", plus they are inexpensive, easy to handle, fun, and can be easily shoved off a sandbar in cases of groundings.