Mastering Python-foo is still on my todo list, though. As a Ruby user, I've noticed that Python scripts are much more straight forward and maintable. I still write my scripts in Ruby though because nobody seems to mind. This is perhaps because I try my best write good comments. In general, Ruby is better as Perl replacement than a Python substitute. In fact, one of my coworkers who is an oldschool perl scripters was sold on Ruby over Perl just by reviewing one of my scripts. I think the issue is people don't think of Ruby outside of Rails, where it's basically a readable purely object oriented Perl.
As an aside, I think there is a bigger overall problem of using scripting languages for application development. I wouldn't use Python, Ruby, or Perl for anything that was more than, say, 500 lines. I almost cried when I tried to read the code for homebrew. Not that it's bad code (it's quite good actually), it's just way too much duck typing for me. I could never keep all that type information in my head. I prefer to pass that cognitive load to the compiler.