I'm not sure I'll make Gillette this year. While I enjoy the rally and the socializing, I can probably get the same going to smaller rallies and doing some "adventure riding" on my own, or with a small group of friends. I don't have a problem with the distance to Gillette, and the riding directly around the rally area isn't a huge deal for me, either. I didn't do much riding when I was in West Bend, actually (but lots afterwards).
Still, the route from Toledo (assuming I'm still living here in July) to Gillette is 1,289 miles. Lots of flat land between here and there. I also don't know that many of my riding friends are going, so that's a LONG boring ride. Give me some terrain changes and my opinion would probably change. It's not the mileage but the scenery. I see corn fields around here enough, already.
To the original question: Better riding on the way there OR a shorter ride (take your pick) would get me there if I was "on the edge". Possibly good riding companions would work, too.