Jim,
I bought a 45 da in Mich City IN and took in to Cleveland (left day after Memorial Day in 2004). Didnt have one bad day of boating the whole way over except for the last hour-and it got bad. I understand it can turn quick on you and the whole key to bad weather is the ability to pretend you dont have a schedule and just enjoy the port that you are at a little while longer.
Was really new back in 04, previous experience was a 26 DA in 88-91 and boated in Lake Champlain.
MY log for your part of the trip was MichCity-Saugatuck, Frankfurt (most boring of the spots), Leland, Harobr Springs, Mackinaw. And, for stopoevers, my wife enjoyed Sauga the best--I liked Leland--harbor and mack i were close runnerups.
I think the key for you is to get north as fast as you can and then spend most of your time from Leland and all poingts north.
I was all marinas and would have enjoyed the islands ( Beaver, Manitou, etc) if I had a dinghy as knew how to use the anchor.
guess beaver has a marina so no anchor issues there.
By the time SLW is done planning his trip to Charle, he'll know those stopovers from LSC to Charl as well as anyone and just stay tuned to this thread.
All the best in planning it.