Earlier quoted context omitted.
I don't really know Python's community that well, but I would wager it's probably due to sheer size. I disagree with PG's "law of averages" regarding choosing environments - working in a language that has more users does have significant benefits in my opinion. BTW another example that comes to mind regarding beginner-friendliness is how long it took to get Rails working with Apache. Before Phusion you were supposed…
I'm not qualified to respond to your points about Phusion and mongrel but on the previous point about the size of the community, are you also finding as a result that the job market for Ruby positions is sparse (forgetting about the economy for a second)? That's the impression I have from the job boards but you work in the field so maybe you have a better idea.
It seems to me most Rails jobs are either for companies who chose Ruby because they really know their stuff, which is great, or companies who chose Rails because 2 years ago it was touted as some sort of Web app pixie dust in Wired Magazine, which is often less fun :)