Haha, to be fair life conditions stopped me from fulfilling my lifelong dream of attending the University of Illinois (i.e., I was an out-of-state applicant who DID manage to get in but was a pretty "meh" student so the tuition was out of our price range), so my anecdotes here are from visiting multiple times over the years ... so my take is probably one of the least valuable on the forum.
With that said, I think something that both makes Champaign awesome but ALSO kind of hurts its development in this sense is that Campustown and Downtown are so separate. As I have said before, I spent much of my life in Iowa City, which comes across as the polar opposite of Champaign in many ways. Whereas Champaign has a gorgeously planned, architecturally consistent campus and a very "manicured" feel to the campus area, Iowa City has its "campus town" and "downtown" as one big hodge-podge, and it seems buildings were randomly put up around Iowa's main version of "the Quad." As a result, I think Illinois has a much prettier campus than Iowa overall, but Downtown Iowa City is a more fun environment with a bit more character than Campustown ... pretty much imagine if you combined Downtown Champaign with its nicer restaurants and cool breweries/bars into Campustown's college town feel and it was all right next to each other. Sometimes I prefer Champaign's setup (when you want to go get a nice dinner downtown in Iowa City at a cool restaurant, you are literally in the middle of all the student bars, too ... and it gets old), and sometimes I prefer Iowa City's setup (my wife and I have been at Legends for a beer before and decided we wanted to switch up the vibe and go to more of a Blind Pig-type setting ... and it's always a bummer that we pretty much have to Uber back).
All in all, I think the perfect medium would be what it sounds like Green Street was like back in the day. I think part of the reason outsiders tend to underrate (IMO) Champaign is that people often judge college towns on how much "charm" they have, and Green Street is definitely starting to have more of a new/shiny look. Again, I still really like it, but I do hope some more unique bars or restaurants go in there over the next couple of years. Even a tiny addition could make a big positive difference, IMO ... just imagine plopping down an identical Blind Pig location where one of the fast food locations is on Green Street; it would be a really cool addition for the atmosphere. Again, though, I cannot stress enough that I love Champaign.