For learning Pharo (while not working at a company), I've learned that going to ESUG [1] and Pharo Days [2] (2 conferences) is the best way to actually learn. On ESUG there are many professional Smalltalkers, including people that write Pharo. And on Pharo Days there are many OG Pharo devs. They can teach you certain things much quicker than any course can.
For example, on ESUG, I was shown how to write a debugger extension on the spot for a particular debugging case (with animations) that had no good working debugging support yet. It was amazing to see how quick people can develop it when they have strong knowledge on it. The fact that the language is inspectable helps a ton.
Another way to learn is by asking many questions on their Discord channel [4]. The community seems really active there and I found them to be really friendly. The Pharo website [5] sort of understates how active their spun off communities are as they simply mention that they exist, but the site doesn't really convey the vibe of how lively the communities are. I'm not sure how one would go about that, but it's a shame you can't directly see that from a website.
[2] https://esug.org
I also fear that leaning so heavily on a closed, corporate platform like Discord as the community hub may lead to tears in a few years. If you're leaning into the idea that "the community is the documentation," you're at Discord's mercy for community sustainment, on top of the already hairy problem of surfacing solutions from within the depths of a long-running discussion forum. Sure, running everything off of mailing lists + IRC like older open source projects do would be a clear step backwards, but being stuck with Discord has been a mild turn-off for me.
Finally, it's worth noting that development is spearheaded by folks in France and Latin America for whom English may not be their primary language. That doesn't affect their ability to do good work! It's totally worth reflecting on how something attempting to approximate natural-language programming in English ended up forked outside the Anglosphere! But I also feel like it'd be worth having an editor take a cleanup pass at future versions of the main ebooks. I've got both the books that Alexandre Bergel published through Apress, and they're both solid, but if the first-resort resources were up to the same standard, I think perhaps fewer people would come away with an unfavorable impression. Of course, that's over and above simply keeping them up to date as development progresses - I believe Pharo by Example is still on version 9?
I assume that step 1 towards parallelism, at least on the image side, would be going through the class library and making sure everything is thread-safe. I'd love to know where one would even get started with that effort. The Roar project claims to support Pharo 1.2, which doesn't seem to be very far after they forked from Squeak, but obviously a lot has changed since then. And the challenge is that Pharo is still rapidly developing all the overhauled classes that distinguish it from Smalltalk-80.
Meanwhile, if I want to play with parallel image/REPL-based programming, I can go over to Common Lisp and, while lacking an equally coherent GUI, be able to load up bordeaux-threads and off I go.