"I'm almost ready to just give up on Perl. After all this time, you'd think this stuff would have gained more ground in the usability space. Problem is, all the Perl geeks who use CPAN use it enough to remember all the tips, tricks, gotchas, pre-reqs, etc."

This isn't a perl issue, it's an ActiveState issue. If you want to make life difficult for yourself while working on a Windows platform, use ActiveState. If you want to make life easier use Strawberry Perl. The compiler issue you mention is well documented, even by ActiveState standards. Basic research would have found this issue before installing the product. Strawberry perl ships with everything you need (regardless of 32/64 bit builds).

"So y'all have only improved the stuff where you have felt it was needed."

Again you're talking (well complaining) about one commercial product, not Perl. Have you raised these issues with ActiveState? I doubt it. I'm curious as to what improvements you helped make in these areas, rather that point out where you (mistakenly) believe others have concentrated their contributions.