|Problems? Is your data what you think it is?|
"So Perl started out on UNIX, maybe it's time to loosen the ties?"
For the love of all that is good and wholesome, no! Under a *nix, developing Perl (and pretty much anything else) is soooooo much easier and better than under Windows. I am not trying to be a bigot (although I am probably being one anyway), but under *nix you have a real Command Line Interface in which you can use utilities like man, grep, tail, and perldoc to accomplish what you need to do in a more efficient manner. Plus you have multiple terminals (which you could have in Windows, but it would hog the task bar and screen in addition to the fact that it would be more difficult to keep track of the content on each terminal).
It's not really *one* thing or another, but many little things that make *nix a better platform to develop on than Windows.
Perl's association with UNIX is important because some of the functionality and use of utilities in *nix has carried over into perl itself. Grep (and regular expressions) for example. In addition to this, Perl culture has been influenced by *nix culture enough that it is important that we not forget our roots. There is no reason why Perl should become more disassociated from UNIX.
As for the quality of the docs, I think that the majority of the docs are fine as far as quality is concerned. Some are a bit misleading or are not as clear as I would like, but that's the nature of the beast. With as much documentation as Perl has, you cannot expect it to be perfect.
On the format issue, I don't know why you are so attached to the pdf format. If you want to print out some docs, nothing is stopping you. If you want docs with links, then docs are also available in html form. I don't understand why this is such a big issue for you.