Good Books

perldocs itself is a good start: http://perldoc.perl.org/index-language.html

Though I have some familiarity with Linux, would it help if I learn Perl on a Linux Box?

Not from my point of view, first you need to get familiar with the language, afterwards you can think of different OSes. The differences are mainly paths and especially packages, some packages are considered Linux/Posix-only, but the most important things are available in both worlds.