Give the answers to "needs" questions, I'd look for an used Albacore or something like an O'Day Javelin or Day Sailor. All are easy to trailer, and for a couple of grand, you could take a cooler, two people and yourself. You'd have both a main and a jib, so you'd be learning skills that translate to larger boats, and you'd have more room to stretch out. The Walker you are looking at is essentially a yacht tender (think rowboat) with a small sail added. You'd have your knees in your nose most of the time. Do a Google on the three I've mentioned above (they will probably lead you to other ideas, too), and then take a look at Craig's list, eBay and so forth. Good luck.