There is always the wonder of ActivePerl (from ActiveState) which works under Win32 (Win9x and NT) and which can be plugged into IIS or run standalone (also as CGI under any Win32 webserver).

That way J'oe could keep his Win32 environment and you could use Perl for your scripts - even in ASPs, if that's a matter.

Note that the Penguin is not the be-all end-all thing, and many people are rightfully reluctant towards the Penguin because of its followers - be careful and know the Linux-Advocacy-Howto if you think about promoting Linux. But I think promoting Linux is plain the wrong path. Perl and administration is always the question of the right tool for the task - and Linux is just a vessel Perl runs on, just like Win32.