An obvious advantage of Perl is that it's cross platform, so you can use the same code on all machines. (However, depending on what you want to accomplish, the way to accomplish it may itself vary between Linux and Windows, so that may or may not end up being an actual advantage.)
Consider Strawberry Perl (rather than ActiveState), it's considerably more streamlined these days.
Consider installing CPAN modules on one machine, and make the site_lib available over a network drive for all other machines (set the PERL5LIB environment variable to add it to the @INC directories). Hmmm... will this work for login scripts? Not sure.
Look into the Win32::OLE module for interacting with Windows specific things.