One minor bit of criticism - would be it be so hard/expensive to hire a designer to do some minor touching up of the DrRacket GUI? It looks like a toy, and the icons didn't even look good in 1998.
I'll balance this criticism with the remark that any language/platform that manages to a) add, ex-post, a type system, b) fix the Gordian knot of modules and macros, and c) has the audacity (combined, curiously, with humility) to just swap out the entire backend to eek out more performance, deserves my respect. In addition both Flatt and Tobin-Hochstadt give excellent presentations where it's impossible not to notice their passion for Racket. They're definitely among my nerd heroes right now.