Darn darn darn. Put together a long post with pics, but forgot to Submit it. Here's the short version: Sirius and Tanzer are both sold, affordable nameplates popular in the Great Lakes region. The Sirius 21
is a lively, solid, quick cruiser with surprising space below. Easy to singlehand; can fit a young family for a long weekend:
Tanzer makes boats from 22-26
that might fit your needs. Tanzers are heavy, robust, surprisingly fast ... and kinda funny-looking. That's partly because they stress interior room, especially headroom, over aesthetics. The T7.5 is one of the biggest small boats out there:
The 25 & 26 are harder to launch with their keels. Good values, all of them. You'll need a big vehicle to tow them.
Finally, look into the Ensenada 20
, a cute little bug that has a large (if obstructed) cabin, often w/ pop top. Small sailplan means it's a bit of a slug, but it toodles along. Lyle Hess didn't design bad boats. Very stable & reassuring to new sailors. Fast to set up, easy to launch. Can be had for under $1200, sometimes.
Cheers, and keep us updated on your search!