As far as the windows trouble goes, have you tried Strawberry Perl: http://win32.perl.org/wiki/index.php?title=Strawberry_Perl
The purpose of the Strawberry Perl series is to provide a practical Win32 Perl environment for experienced Perl developers to experiment with and test the installation of various CPAN modules under Win32 conditions, and to provide a useful platform for doing real work. It's in alpha at the moment, but I'm sure they'd love your feedback. Also because it's designed to be unix-ey on windows, it's likely to play nicely with Catalyst which as you noted is biased towards the unix way of doing things.
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