Jesse Alama here. If you bought a book from me but are unsatisfied, I'm happy to refund you. If you found my stuff unhelpful, let me know what's missing and I can try to include a discussion of that in the next edition. Just write me offline. Or write to the group, or visit us (or me) in the Racket Slack.
I wrote my stuff to help people get into web development with Racket. I love web devel, and Racket, too. You and I have a lot in common: I found the official docs puzzling, so I worked out my own approach to them and made _Server: Racket_. It should go without saying that that's the origin story of just about every paid book out there on applications of programming language X to domain Y. That's not even a criticism of the Racket docs. Plenty of tools/languages also have good docs, and there are lots of books, too. How many Django books (or even courses) are out there?
There are also some great web programming tutorials out there for Racket, too. I recommend this one, by Racket star Jens Axel Søgaard: https://github.com/soegaard/web-tutorial .
I hope you'd give Racket a chance. Since you're talking about it, it sounds like you're dipping your toes in the waters. I'm pretty sure you'll find them quite welcoming. That said, all this negativity is pretty off-putting.
I used to (and sometimes continue) to think that way, too. DrRacket does look terribly retro or unpolished at times. But despite appearances, DrRacket offers unique power tools for working with Racket programs that's hard to replicate at the terminal or in Emacs/Vim/etc. I work with multiple (Racket) languages, and DrRacket shines there because it supports Racket's "multi-lingualism" out-of-the-box. What's also not immediately visible is DrRacket's extensibility. Take a look at Laurent Orseau's quickscript (https://docs.racket-lang.org/quickscript/).
Sperber is an amazing speaker and fantastic programmer. This is a great talk. He'll be talking about similar things at Racketfest, the Racket conference I'm currently organizing (https://racketfest.com). The idea is to build on what are called design recipes, a brilliant idea (or family/scheme of ideas) developed by core Racket guys (see their How to Design Programs [https://htdp.org]).