A guy I used to know from another forum has done Michigan <-> Winter Park by train several times (also through Chicago, I believe). He said one strike against the train is the return trip Colorado -> Michigan. Apparently the train on that route originates in California. If there are any delays along the way from California to Colorado, that affects your departure time at Fraser. He mentioned having a scheduled departure at Fraser for 11:00 or so at night that had him staying at the train station until 3-4 am.
Me, I'm doing a family driving trip to Colorado this summer from Michigan (Detroit area) as a test run to see how bearable/unbearable it is -- to gauge the possibility for future snowboarding trips to Colorado by car. My kids (5 and almost 8) are excellent car travelers, but Colorado will be two solid days in the car for us -- 20ish hours to Summit County I think. (I don't drive overnight.)
Sooner or later your legs give way, you hit the ground.