Your points about documentation are well taken. There seems to be a dissonance between the mainstream world and Pharoers in this regard. Mainstreamers pretty much expect documentation to be good and to be reliably available via the web (I expect this myself in most cases). In the mind of a Smalltalker, there's no need for a web page that lists classes, methods, and what they do because that's precisely what is available inside the image and what many of the built in tools are there to provide. Now, is that good enough? Clearly not. Outsiders might not know this is the case, especially if they are coming in completely blind.
I think it would be not too much work to parse out this kind of information (Class comments, methods and method comments, structure etc) and spit it out as a web page that could be hosted somewhere. Do you think this would help, at least somewhat, to bridge the divide with new users?
Your suggestion of parsing out the in-code documentation would go a long way towards documenting the libraries, provided the documentation is of high quality. However, that still doesn't address the bigger question: how do I program in Pharo.
There's a book, "On to Smalltalk" that actually did a decent job of getting you started, but it's decades out of date now.
I think it would be not too much work to parse out this kind of information (Class comments, methods and method comments, structure etc) and spit it out as a web page that could be hosted somewhere. Do you think this would help, at least somewhat, to bridge the divide with new users?