What to buy for $5000
If it was me, I would go to an older Catalina 27. You had one before, and know the boat. While not the most solid boat ever built, they are great boats for the Great Lakes. One has even circumnavigated the globe.
They are inexpensive, sails and other equipment are easily and economically available. They are good sailing boats and offer a lot of interior room for the size. How can you go wrong? Because they are such good boats, a lot were sold, and that means there are many available on the used market. For a temporary solution I see it as nearly a "no brainer".