I agree with Ofreen. I saw a lot of people sign up then bow out at the last minute last year. I know I was only able to do the Chicago part of the Chicago to Indy part last year and we almost didn't have anyone to get GZ down to Indy.
It's well and good to want GZ to get everywhere by bike, but sticking to that last year did cause problems when he got hung up around New York because there weren't any rider willing and/or able to ride during the week to get him to Canada. The Michigan leg that I also participated in was pushed back a couple weeks by that.
My schedule is very flexible, but I still need a decent lead time to schedule a multiple day vacation. Most people can't change the dates of a 3-4 day vacation with only a week's notice.
I think decent date certainty for the various legs will help with participation, and that may mean that GZ 2.0 will accumulate some frequent flier miles with UPS or FedEx. In the end it's about we riders getting together to ride and make some new friends, not just running up GZ's mileage totals.