Re: looking for a small sailboat
Having gone through this same process only a few years ago - I would agree with both Krisscross and JustinB. Much, much better sailing in a 14' sloop-rigged dinghy - but if roof-topping is a must, then you might want to pick up a Snark. The Snark is common enough and cheap enough (used) to give it a try without reservation. Lot's of used ones around - I paid all of $100 for mine, which included a fairly new sail. Pretty cheap toy/experiment.