In earlier discussion of a draft, a year ago, I looked at a bunch of examples, and zeroed in on Nim's home page (at the time) as a possible good example/inspiration for Racket (especially since I was pushing on a "3 ideas" focus, which, IIRC, Nim was also doing):
https://groups.google.com/forum/#!topic/racket-dev/kJciZheDM...
I think a few pretty ordinary challenges are:
* Collectively, people think a lot of stuff is important, and don't want to drop it from the home page. A vicious designer would step in and cull and massage heavily, ignoring the screams of pain from most people. (Only in the end, might people generally agree it was worth the suffering, and then they'd help beat down anyone who tried to sneak bloat back in, after the carnage that everyone went through to get there.)
* The people in charge and doing the work on the site, as a group, don't have the same ideas of what's important that professional practitioners do, nor the state of competition. So, priorities, phrasings, assertions, etc. will sometimes seem odd. This has come up at least a few times, in various ways, and might be part of why Racket didn't go mainstream when it had a better chance. (Though the leadership is not just pure academics. Just to pick the most prominent example, Prof. Matthew Flatt, besides the research and domain background, is a very solid programmer, with some good sense of software engineering.)
* As a subset of general visual design, good graphic designers seem to do many subtle things that us techies don't fully appreciate. Familiar analogy: a novice software developer not only isn't yet able to do great work on tricky problems, but they don't even yet know what great work is, nor are they able to say what's great and not about some example they see. (The creators of the new site are mainly programming language and CS education people, not visual design, not HCI, etc., except sometimes people like [1].)
On the upside, if a site for some techie thing looks a bit homely or awkward in some ways, you know it's at least not a tech offering driven by marketing, fashion, and funding. :)
[1] One notable exception in Racket, though I don't know whether involved with the new site, is Matthew Butterick, as a diversely multi-skilled person. He did a lot of visual/graphic design work on other Racket stuff, which you can see by contrasting the old look of the documentation, with the current one. Old: http://planet.racket-lang.org/package-source/neil/roomba.plt... Current: https://docs.racket-lang.org/roomba/index.html