Encouraging words, @marlowe1 ! But I am curious, what is your view of the financial history of the University? We may be looking at this through different lenses.
Here’s my view: buoyed by one of the largest higher ed donations ever (from Rockefeller) UChicago started hot out of the gate in the 1890s (pesky Chicago fires aside). Within a generation, they emerged as one of America’s top 3 research universities, with an endowment to match. (Harvard and Yale were probably the two others, although Michigan and Wisconsin were strong.)
The school’s financial health dipped during the Great Depression - like its peers. It did enjoy some war-time momentum, again, like its peers.
The late 1940s is when the divergence started. While its peers enjoyed a post-war boom, Chicago went south. For a variety of reasons (some you mention), the school enjoyed almost none of the GI-Bill related benefits found at other great universities.
The endowment went south, too - falling from the top 3 into the teens. Sadly, the school has never really financially recovered from the post-WWII struggles.
Buoyed by new ambition in the Sonnenschein/Zimmer era, it took a risk to finance eminence with debt during the 2009-10 Great Recession. The debt financing led to forward momentum in the 2010 decade, but COVID times threatens this greatly.
My view is the University is still recovering from the financial wreckage of the 1950s. COVID could lead to a steeper, downward turn for Chicago quite quickly.
My fear, frankly, is not without a comparator. If the U. takes too many hits, I fear the University will resemble UChicago Medicine - a once eminent hospital system (in the top 10-15 in the nation), that sustained decades of struggle, and is a shadow of its former self.