I've been using this https://gist.github.com/1548742
to generate package skeletons for django apps. Configures a django-nose test runner for setup.py, package data sniffer, etc.
I wouldn't count the need for a good JVM implementation as a plus mark in a Ruby vs Python comparison. Jython is used when you need to interact with Java libs, not because the C implementation of Python language is slower than the JVM one. The same does not apply for Ruby, you use JRuby because it's better than CRuby. If you want to compare speed you'd be up against pypy.
You've just echoed my experience with chef but I'm still on the fence as to whether I think it was a success or not and whether I'd use it again. We were able to achieve everything we wanted but to say it took a metric fuckton of time would be a grave understatement. Even what are ordinarily trivial things took a lot longer than I expected. Some things I just found to be oddly designed and surprisingly inflexible, especially the recipe construct. I still to this day see no point of having a folder with 2 subfolders with 3 files combined for what amounts to "apt get install somepackage". And having to learn a DSL to replace the already very effective bash is in my opinion not a very enticing trade.
Although it's very new, I think I'll try out juju.ubuntu.com for my next large deployment instead of sticking with chef or puppet, if only for the flexibility of the hooks-in-any-language thing and a chance to feed my bash fetish.
Depends, if I look at my local job listings where there's one ruby listing for every 10 python ones I'd say different but I'll admit that that ratio is abnormally high but indicates that the same trend governs most places bar Chicago. However, if I look at HN submissions, it's almost the other way around. Given that I've worked in three countries in the last 5 years and noticed the same trend in all of them, I am starting to think that Ruby developers are simply more evangelist.