I have very few issues with Ruby as a language, in general it let's me get from thought to working code quicker than any other language I've used. Honestly the largest issues I've run into with Ruby typically deal with people trying to be too clever.
Ruby certainly provides a lot of ways for people who want to look incredibly clever to hang themselves and anyone using their code. I typically avoid libraries or frameworks where clever code is the norm (I'm looking at you Rails), and because of this I tend not to have too many problems.
It's certainly not perfect, and I've been frustrated by bad error messages, stupid type system mistakes, etc. But I've found that those issues simply replace issues in other languages.
I still feel that Ruby gets me from Thought to Code quicker, and for the kind of projects I typically do, that's worth dodging a couple of warts.
-> "the largest issues I've run into with Ruby typically deal with people trying to be too clever"
I agree with you about Thought-to-Code and even though I argued in favor of monkey patching earlier, the willingness to use it without discipline has raised a red flag for me and is the biggest sign of this "too cleverness" that you're referring to (at least for me). If Ruby becomes the new Java, maintaining irresponsibly monkey patched legacy systems could be a nightmare for the enterprise developer in the years to come.
I love Ruby. I love that code can be so short and yet easily readable. It might be slower and perhaps more memory-hungry than other languages, but for my needs that's usually not an issue.
What I do miss are good, well documented, stable libraries. For example, I currently process RSS/Atom feeds with FeedTools, whose own creator says he's tired of maintaining (I totally understand him and am extremely thankful for the time he put into it). I assume if there were more people coding Ruby, there would be a better chance someone would step up and take his place. So, having a community that is more welcoming to newcomers would eventually benefit us all.
By "open to newcomers" I don't mean that Ruby-celebs should stop posting snarky comments at each other in their blogs. This is pretty negilible. I mean stuff like having better documentation, for example, online, free, in googleable format (rather than screencasts or print books). IMHO PHP3 annotated online docs back in 1999 were significantly more usable than what Rails has to offer now.
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 to run your own mongrel cluster or similar fringe solutions - it was insane to ignore the world's most widely installed server. Personally I only started considering Rails production-worthy after mod_rails turned out to be fast and stable. Sure, I can run Thin/nginx or whatever, but I don't want to learn a new server (and wait for it to mature) just so I can use Rails.
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.
Actually, there's plenty of Rails work out there, and usually in higher rates than PHP (granted, you do accomplish more work per Rails hour).
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 :)
I wasn't sure whether the latter firms had found some new pixie dust by now. Good to know. Obie Fernandez has a talk online somewhere about billing where he says something like no one working in Rails should bill less than $150/hour and that he bills himself and his developers at $250 but will occasionally give discounts for various reasons. Maybe I have numbers wrong - just found it - http://www.infoq.com/presentations/fernandez-sales-do-the-hu...
I recommend watching it. Good talk. Takeaway point - always err on the side of charging too much :)
I am not happy with them: recently I was looking for the API docs of the standard library for Ruby 1.9, and it turns out it is not available online anywhere. ruby-doc only has the 1.8 stuff. I spent hours trying to figure out how to create my own documentation with rdoc ad ri but eventually gave up. So now I don't even have the documentation of the standard library for Ruby.
ruby-doc.org is nice, but there's a lot missing in the package level (FeedTools etc). Also, it could use a lot more code examples.
Here again I think it's interesting to compare to PHP's annotated docs ca. 2000, which were a great resource since they usually contained a few common usage examples for every function. The language itself was less consistent and mature than Ruby, but the user contributed (pre-Web 2.0! ;)) docs made up for it.
