I wonder what happens to those Perl hackers who write a lot of Win32 modules. I've submitted quite a few to CPAN and I worry about my job prospects, especially when I see job ads on jobs.perl.org that say "If you have Windows experience, we will not hold it against you." Ouch.
I've been working on Win32 support for my own (Ruby) modules and I've been getting to know the Windows API more detail as I go. It's not nearly as bad as I thought it would be, I have to admit. I'm finding that there just aren't a lot of folks who know Windows. This can work for you and against you.