The Reply
Here's the reply from my message to the Office of Housing and Dining Services. It is interesting, but perhaps logically flawed.
Dear Adam,
Thank you for your message. We believe that our House Table program, or residential dining, is the cornerstone of our House System. We value them greatly, as we think that students' ability to feel connected in the House System is due in large part to their being able to eat together in the three dining commons that we operate. However, it is quite inefficient for a housing program our size to operate three separate dining halls, as a campus our size would typically only have one dining hall to serve this number of students. As a result, students who take meal plans pay for more than the raw food costs, but also pay to cover the associated costs of having our model of a dining program - the staffing of three dining halls, the facilities upkeep and maintenance for three dining halls, etc. It would not be feasible to operate our current system otherwise. Just like at a restaurant you don't pay for the pure raw food cost, neither in a residential dining facility do you only pay for the food - you also pay for the dining operation that produces the food.
Please let me know if you have any additional questions.
Best,
Ana

The logic of that depends on the price of the food. I know here, food prices seem to be inflated, and I imagine the extra money goes to facilities and maintenance and the like. All restaurants have the same dilemma, and put that added cost into the food. So if your food is relatively cheap, then it makes sense, but if it's comparable to a (relatively cheap) restaurant, then that sounds like a formula response to typical student inquiry about prices. Also, it doesn't really answer your question about dining inequality, making the latter seem more likely.
And as a comparison, freshman here have to get a minimum plan for $2,126 a semester with 230 club meals (which usually translates into a meal) and $400 declining balance (like your flex). We also have 3 dining halls and a comparable student body (I think), although each one is relatively small.
The crux of the matter, which no one would know unless they attend Chicago, is that the 900 "dining points" are precisely the same as dollars. There is one dining hall where they may be used, and they decline exactly like dollars. Moreover, one can actually use normal money at this dining hall. So one could therefore have no dining plan and buy the same amount of food for $500 less per quarter than with a meal plan. Why this "overhead" is not simply built into the price of their entrees, and extra dining points given out to compensate, is beyond me.
Thankfully (well sort of), I'm not assigned to that dining hall. Instead I have a large number of "meal points" (i.e. all you can eat) for this place attached to my dormitory. It turns out that the equivalent cash price of my meal plan is more than I actually pay for it.
There's only one dining hall where they can be used? That's kind of weird. Here, you can get everything with "declining," including all-you-can-eat meals. Basically, it sounds like your system is messed up, and dining services does't want to admit it.
Meal points here are also (usually) cheaper than the cash price for meals, but get more expensive when you get smaller meal plans (which I guess makes sense). But most people don't use up all their meal points, and they don't carry over, so the extra is just free money for dining services, basically. That's a bit of a contention.
I think you're correct on both counts. Your system seems to generally make sense, at least from the perspective of the office of dining.