Push the easy button for this one. While there are quite a few different brands I can say from experience that an older (I think they made them untill 1995) Macgregor 26S (swing keel) can be had for that price, many probably lower. We love ours although we are looking to go larger very soon. We will miss a lot about our little trailer sailor like the ability to beach it, dock almost anywhere, low slip fees, not having to schedule with the travel lift, the ability to bring her home during the off season, the ability to pull her out when a hurricane is on its way, etc.
The older 26D (dagger board) can be found even cheaper and I've heard they sail better than our 26S but I do prefer if we run aground having the swing keel simply swing up.
You'll hear a bunch of negative posts about Magregors but they are mostly from people who haven't even been out on one. Our little boat leaves the slip a few times a week passing large expensive "proper" boats that sadly sit tied up growing barnicles and slime. We also find ourselves heading out when the white caps are starting to form while many larger boats are clearing off the bay, its no storm chaser but we've been in weather where we actually surfed her into a creek to
anchor for the night which was a little hair raising but the boat did well.
We just put her in Friday evening and so starts another great year of sailing! Even after almost 3 years of ownership I still have a hard time leaving the pier when it's time to go home.