A little bigger boat
There are a large number of Ericsons on Lake Michigan as many were sold out of Larsen Marine across the lake from you in Waukegan. The 80s vintage 27, 28, and 28+ are very solid, good sailing, well-finished boats that could be had in your price range. There are quite a few on the lake. (Also a very large online owners community.) Good luck in your search for your next boat.