I have another long trip planed for July/Aug, I'm taking the Road King out to Pikes Peak, and if time allows the Grand Canyon, and I may take another week to ride the back roads in the Black Hills on the new DR 650, so a long ride out to Deals Gap isn't something I need to do, I would if that's what everyone else wanted, but it didn't really sound like it was written stone for anyone. Hope I didn't step on anyone's toes by suggesting SW Wisconsin.
From what I hear, there is a section down there that has been described by some as the Dragon of the North (i think it's SR-171 on the link below), and even though we might have less total miles by staying closer to home, we should get more quality miles by going that route.
Wisconsin Motorcycle Roads Look here for more info on the area.