you can skip Rework if you want. It's not about the hard tech skills, more of the soft skills. It's just a book I read recently
and think that it had a lot of really good things in it to improve the soft / business skills, which should help someone stand out in the long run.
As for Counter Hack Reloaded. I agree it's great. I'm about 1/3 of the way through it, it's sitting on my kitchen table next to my box of books on hacking. (Note not in the box).
I could toss in a few other books too, but since gt86 is just starting out, there are some basics first.
Notice my list was mostly about OS, Networking, Best Practices, and admin type skills. For a list of hacking books:
Hacking for Dummies (More best practices / overview of some tools, but liking Dissecting the Hack better for that now).
Hacking Exposed: Wireless
Counter Hack Reloaded
Professional Penetration Testing
Courses / Certs:
Sec+ (recommends 2 years experience in admin and networking)
OSWP / WiFu
OSCP / Pentesting with Backtrack