@JBStillFlying - I doubt the endowment tax seriously inhibits the school’s desire to grow their endowment. It’s an annoyance, no doubt, but I anticipate the endowment managers’ main directive is to grow the endowment as strongly as possible.
Also, I agree, Chicago has done more with less, but sometimes, more is more. Especially as running a U. gets ever-more expensive, larger payouts from the endowment can’t hurt.
(Additionally, keep in mind that for the first 70 years of its existence, Chicago had a top 3-5 endowment - it’s place as a financial middle weight, by institutional standards, is a bit more of a recent trend - since about the 80s or so.)