Good Books - Any suggestions or pointers would be immensely helpful

"Mastering Regular Expressions" by Jeffrey Friedl and "Higher Order Perl" by Mark Jason Dominus (free ebook available for the latter) are the two books I would strongly recommend.

Though I have some familiarity with Linux, would it help if I learn Perl on a Linux Box? Is there any advantage in doing so?

There are lots of perl functions that map pretty much directly to syscalls on linux, but which are usually awkward or not implemented on windows (for example handling symlinks). See for example the sections "Input and output functions" and "Functions for filehandles, files, or directories" in perlfunc.

If you want to learn to use those, doing it on linux would make things much easier. On the other hand if you plan to stay on windows, there's not much point.

A very good way to become a better programmer (not just perl) is to participate in the community (for example sites like perlmonks and stackoverflow). That way you get to read some code that other people wrote, plus some suggestions on how to improve it, and some tricks for implementing things that you would never invent yourself.

An even more direct approach would be to find somebody who reviews the code you write for work, and gives you suggestions on how to improve it.

Foremost apologies if any questions asked here appear irrelevant.

They aren't. Similar questions have been asked before, but right now I can't find any similar nodes.