One of the biggest problems is that these language designers, who want to design an "idealized" language, continue to make big decisions without regards to any kind of actual data collection. I just had the chance to meet and talk with Andreas Stefik, who summarized the utter and embarrassing lack of research by the PL community about actual language usability[1]. I'm not exactly jumping into line to adopt his evidence-based language "Quorum", but thank goodness that someone cares enough to do actual HCI research instead of just arguing theoretical merits. My own history and feelings about Racket are with regards to its connections with the controversial "Program by Design" curriculum - feelings that are both complicated and narrow (all revolving around introductory computing contexts). But I certainly resonate with this quote from the article:
"But in the last 60 years, simply grabbing these dissenters by the lapels and fumigating them with the stinky garlic breath of parenthesized S-expressions has not been a winning strategy. If Lisp partisans want different results in the next 60 years, we need to try something new."