I'm not sure I agree that that there is clear winner in expressivity between Perl and Python. In Perl dealing with nested data structures feels really awkward.

I'm not sure I agree that that there is clear winner in expressivity between Perl and Python. In Perl dealing with nested data structures feels really awkward. And Python's list and dictionary comprehensions and generator expression are very handy and highly expressive. Anonymous functions are much more pleasant in Perl than in Python. The added flexibility in placing 'if' and 'while' in Perl is nice sometimes, but I don't think it is a huge advantage. Going over this (personal) list made me realized I'd probably like Perl 6 better than either Perl 5 or Python...