I bought one of these in the middle of last summer, and sold it by the end of last summer. I took it out 3 times, and just wasn't comfortable with something that old. There was a lot of flex in the CB trunk and there were some places (on the "deck" that covered the bow) where small tears were developing in the fiberglass where it attached to the hull. It comfortably fit 3 large guys, and handled pretty well in moderate wind, but there was a lot of spray coming over the bow/gunwale (and we were on a mid-sized lake in Minnesota). Also, the cockpit is not self bailing, so if you take on water, you better start bailing. I bought the boat plus main and jib, trolling motor, battery, and cockpit cover for $500 (I already had a good trailer). I sold the boat, accessories, and trailer for $950 at the end of summer (and bought a Com-Pac 16 + 4hp motor for $2000).
If you can identify bad (weak) fiberglass, the boat, sails, and trailer look to be in good condition, and you don't mind getting a little wet, then $1,000 would be reasonable. If it's your first sailboat and you will be sailing alone (or +1) you might look for something small that could easily be swamped and recovered (Sunfish, Laser, Escape) to learn the basics on. That's how the wife and I started, we moved up to the Leeward in the hopes of staying dry, but upgraded to our current Com-Pac 16 because the Leeward just wasn't cutting it. Our first sailboat (AMF Copperhead) took about 15 mins to rig, the Leeward took about 20 mins, and the Com-Pac takes about 20 too.