You might consider the contessa 26. It meets some of your requirements but not all.
On the plus side
- a very safe boat that will handle great lake conditions.
- Price, here in Canada a well maintained co26 will run you about 10-15,000$
- small enough to be handled by 1 - 2 people, including mast stepping(on deck not on keel)
- She will always be one of the prettiest boats in the harbour
- given the fact that she was built in Ontario there are plenty used co26's to be found on the great lakes
on the neg side
- mine is stored on a trailer and quite tow-able but I would not want to launch her via the trailer. She weighs in at about 5400 pounds with a full keel and relatively deep draft for her length
- what you get in safety you lose in comfort, she is small by today's standards with well less that 6 foot headroom
- the most popular engine is a 7.5 hp ferryman, very reliable but vibrates like crazy and parts can be hard to find.
For more info on the boat check out co26.com
(sorry I can't include a link to the site as this is my first post on sailnet and the site will not allow me to embed links in my postings just yet.)
Good luck in your search,