22 works for me
I learned on a 12 foot Topper, and then bought a 22 foot O'Day several years ago. While I do trailer it around a bit, it mostly stays in the water on an inland lake on a mooring. You do a lot more sailing if you don't have to worry about launching and hauling out each time. Dry storage is almost as good (i.e., keep it on the trailer with the mast and boom attached at the marina) and at a fraction of the cost. When you move beyond trailerable boats, the costs do go up quite a bit because you incur storage expenses, launching and hauling, inboards vs. much cheaper outboards, more expensive sails, ... (you get the picture). I've got no regrets. The only serious expense was getting a beefy enough tow vehicle for the traveling around. If I wasn't going places, I wouldn't bother. You can always borrow a tow vehicle, or even rent one for a day.There are some great deals out there. If you feel like you know your way around a sailboat (even a small dinghy), you'll find the transition pretty easy. Good luck.