You raise interesting issues. For instance, I've never seen documentation on cross-compiling with perl and cpan. And testers.cpan's testing of Windows could certainly be more pervasive, and broader (eg, ActiveState perl, ActiveState with their precompiled modules, ActiveState with M$ VisualStudio, gcc-built perl with raw Windows, with cygwin, with mingw, and all under Win98/2k/CE/etc).

As pointed out, some other languages provide better cross-platform and Windows support. Tcl makes it easy to create a stand-alone Windows executable containing a collection of source files which look to themselves like they are living in a normal filesystem (ie, www.equi4.com/starkit.html). Easy even from Linux.

Perhaps perl developed among "people with root access", and tcl among "less privileged users"? Or for "systems you have access to" rather than "tossing apps into the unseen wild". Or for "real" OSes? Or perhaps ActiveState blocked the upstream presure to make perl more portable?

Still, how difficult would it be to create a starkit equivalent for perl...? Perhaps the perl community just isn't trying? ;)