Yeah. In my experience, Rubyists are more likely to be solo developers, self starters and/or be keen to improve things/reinvent wheels rather than necessarily work on "official" projects with all the bureaucracy that's involved. I wouldn't dare to speak for
all Rubyists but, in general, I'd say the typical Rubyist is
very anti-bureaucracy (more so than developers of any other group I've experienced).
There have been tons of Ruby documentation sites over the years and if all that effort had been put into developing a good system for the "official" documentation, it'd probably the best of any language ;-) But Ruby is very "long tail" when it comes to deciding what sites to read, mailing lists to use, etc. There are few de facto points of congregation.
That said, I'm not criticizing, because I'm the same (I want to run my own gigs, not fit in with someone else's system) and that's what I like about Ruby and Rubyists. You don't get a single "official" book of documentation about math, architecture, or English language syntax. Instead, everyone releases their own attempts and a wide variety of viewpoints and coverage is available.
In this way, Ruby feels more like a discipline or "way" of doing things than a single, specified entity that can be centrally documented well.
(I'm talking from a Ruby POV rather than a Rails one, since you brought up Ruby specifically in comparison to Python. Rails has a much more bureaucratic and centralized community than Ruby does. Rails' official documentation is also miles ahead of Ruby's.)