Take comfort from the fact that you are graduating into one of the nastiest job markets in the history of the United States and still don't have to face the kind of competition that you would in any of these countries:
despite his accomplishments, Liu teeters on a mental precipice: "It feels shameful, like, hey, I’m in my early 30s, I should have had a Yahoo by now or I should at least have had a company I sold for tons of money."
If your opening paragraph hadn't been misperceived as the rantings of a sociopath, people who read your second paragraph ("love the one you're with") would have been pleasantly surprised by your insight.
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 :)
You're lucky that in those cases you were able to recover in only two days. The time it takes to get back on track can be proportional to the size of the project so imagine if you were dealing with an enterprise system written in and monkey patched in Ruby and you had a similar problem. Depending on your luck, you might get back on track or you might end up having a lot of extra time to work on your resume.
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.
-> "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.
How do you deal with excess verbosity in C#? I know this is a separate argument from the monkey patching issue but for me the conciseness and elegance of the Ruby syntax versus C# is the primary reason to choose Ruby.
Why? Because of monkey patching, syntax, performance, the community or some other reason such as you prefer Python or have an intuitive, ineffable and unexpressable disklike of the language or because Matz is from Japan and they bombed Pearl Harbor?
Just because it's a satire doesn't mean the title in incorrect. I would argue that Ruby is, in fact, the future for the same reason that Python is the future.
As for monkey patching, yes, it's ill-advised in general just as global scope and gotos are ill-advised for similar reasons. However, monkey patching is a powerful feature if used responsibly as Chad Fowler has noted ("The Virtues of Monkey Patching"):
Now admittedly, not every programmer is as competent or responsible as Chad Fowler or the programming world would be a very different place but the point is there's a right way and a wrong way to do it.
Werner Schuster's article on InfoQ ("Ruby's Open Classes - Or: How Not To Patch Like A Monkey") has more good advice on how to do it the right way:
Liberia (80%)
Zimbabwe (70%)
East Timor (50%)
Bosnia (40%)
http://www.aneki.com/unemployment.html
Graduates in any of those countries would gladly swap places with you.