Comments about the differences between Admissions, Academics, and the Administration are not uncommon anywhere. While all are important to the running of the institution, they all have slightly different goals. Admissions goal is to make the University look like it is Heaven, and to present to the University the very best class it can get. The academics are focused on furthering the Body of Knowledge and sometimes that conflicts with teaching undergrad courses (although it sounds as if it might be well above average for the undergraduate experience at UChicago), and the administration has the non-glamourous task of making sure resources are allocated appropriately to accomplish the goals of the other groups (and Athletics, Arts, etc.).
Often times people struggle with the course of actions that admins take. They don’t often have the same level of “customer service” that the admissions group has. I know when I went to Kellogg, year one was all about the institution making it great for us, and that fell off greatly in year 2. They already had us committed and we were going to finish, but in year one, in order to protect their brand they went all out with events, mixers, etc. to make us want to return. The second year was just “grind-it-out.” My fellow cohorts often commented on how after the first year, we were pretty much forgotten. It is just the way it is. Once you are in the door and the switching cost is high, the amount of energy spent on maintaining their customer, is going to be lower.