From the point of a view of a student in Indiana, prior to the 2015 season (as in Spring 2014), we were under the impression that Illinois and Indiana were going to form a district together. Not sure why that plan changed, but it probably was through FIRST mediating their smaller district trial and IndianaFIRST's and Illinois FIRST's own discussion.
As for coming years, I think that an Iowa/Illinois district makes more sense than Wisconsin/Illinois geographically. The Iowa teams may have to travel quite a bit, but then, when don't they?
Adding Missouri in would also be pretty easy if they wanted it to be a larger Midwest district, since there would be enough teams/events that Chicago teams won't have to go to Southwest Missouri or vice versa. Also, St. Louis would be a great place for a Midwest DCMP.
Obviously, volunteer base would have to be flexible and available for such a large (area) district to work out with a lower team density than, for example, Michigan. Also, I would be sorry for Wisconsin if that district happened along with Minnesota.
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2012-2013: FTC 4601 (student)
2014-2015: FRC 135 (student) - 5 banners in 2 years!
2016-present: FRC 4272 (mentor)
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