1. South gate in Chicago is kind of challenging in general, but for most long distance trains, they board seniors 62 and over first and then families with small children--I would say by 2:30 should put you in reasonable shape.
2. There is one giant overhead area for everyone so it's kind of...
I noted that they forgot to address the Heartland Flyer and also nothing was said about criteria for on time protection for Chicago St. Louis--I bailed on such a mess over the 4th of July when 22 was estimated to be 4 hours plus late at Alton and went out of Champaign instead.
To me depending on your schedule, you might want to consider using the Cardinal on the eastbound trip as it leaves Chicago at 6:45 PM vs. 10 PM. Also, if you are taking the Cardinal, you could also work in a stop in Washington DC as well. The thing about all the east coast long distance trains...
I practically commute on 59 and 392 almost every weekend and one reason I don't ticket by round trip is that if one needs to make changes it's a lot simpler if one has not had the physical tickets issued!
I am from Chicago and have been involved in a number of online activites related to Amtrak for a number of years such as the yahoogroup all aboard and am also part of the groups that NARP has set up for the City of New Orleans and the Sunset Marketing team.
One other thought related to the stickers--maybe a means other than signing up with myspace would be a good thing. I work in a library where myspace freaks out our computers big time and wanted to get one but won't for that reason join myspace.