I think Pharo would benefit a lot from having lots and lots of screen casts, since so much stuff is visual. I don't think something like ESUG is a sustainable way to spread techniques. A lot of stuff that is well documented in the Pharo ecosystem is old. A lot of the new stuff doesn't have great docs. Just reference docs and code is not enough. There has to be a coherent narrative around an API to put it together.
Also, I'm all onboard having a UI environment for programming, but it needs to have great keybindings that follow platform HIGs, and at least my Pharo 10 experience of the window management was really bad.
I wrote about this some https://nikhilism.com/post/2021/experiencing-smalltalk/