Just an idea, how about Visual Perl .NET from Active State, plus the following link: Building Outlook 2002 Add-ins with Visual Basic .NET? I know that link is about VB .NET, but should give an idea on how to write Outlook 2002 plug-in's in .NET.

Another idea is to write the plug-in (COM) in Visual C++ and embed Perl interpreter in it. A lot of work but could be worth the effort.