More ideas on a smaller (not too small) daysailer that's easy to find cheap are always welcome. I'm seeing some 22' Tanzers, Catalinas and Hunters that look intriguing. I'm assuming a boat that size would be a lot more manageable both at the dock and under sail than a 27-footer.
Depends on if you plan to trailer the boat to the lake or leave it on the water. I had a Catalina 22 that we could launch from most ramps (swing keel). However, it took a good 1.5 hours to set-up b/f sailing. And another hour after sailing. We found that once we got a mooring pin, we sailed more. OTOH, you may find a smaller boat that you could get on the water faster.