I've seen a few people comment here that it's important for the route to have more turns or the mass gets too spread out. Just mentioning it--hope it's a great ride! :)
Sure, some "stair-stepping" can be added to the route if necessary.
This was a nice ride! I had to bail at Milwaukee but had a great time. As far as keeping the group together, i noticed the front waiting at a few lights which seemed to work pretty nicely, too.