Welcome to the forums.

I'm going to be brief with my responses because these types of questions have already been answered dozens of times elsewhere, and I encourage you to review those other threads because there's a wealth of information in them.

Job: It will probably be more realistic to land a full-time security position in 2013 than a pen testing position. You may get lucky, but your best course of action will probably be to ease into it a bit more. Landing a position that has the possibility of some internal pen testing activities will greatly help you get into a full-time pen testing position as well.

Certs: You don't need any. If you have demonstrable skills, you can get by without them. The OSCP is great, and the OSCE beyond that. OffSec also has a new web app course/cert that will hopefully be available sometime around the end of the year. SANS/GIAC GWAPT, GPEN, and GCIH are nice ones to have as well. Of course, the CISSP satisfies a check box for many places and helps you get past HR filtering.

OSCP: Most people are short on Linux experience, so you're probably in a better starting place than most. You'll learn the most by experimenting in the labs, so as long as you're comfortable with Linux, Windows, and networking, go for it. Reading through that book list of yours would certainly put you ahead of the curve though. Unless you have a lot of time to dedicate to the labs, you'll probably be best off registering for 90 days at the onset. 60 was a bit tight for me, and I compromised about 80-85% of the systems.

Books: Popular ones you're missing are Counterhack: Reloaded, the official NMap book, and the Wireshark book. The Coding for Penetration Tester's book is a nice one as well. That one helps you think outside the box and take control yourself, as opposed to just showing you how to use tools.

Skills: Besides the obvious, http://www.thehackeracademy.com/the-key-skill-set-of-great-penetration-testers/ and excellent writing skills. I spend about a third of my time writing reports. Internal QA and your clients do not want to suffer through poor grammar, usage, or spelling. Speaking skills to a lesser extent. I typically conduct a 30-60 minute exit interview at the conclusion of an engagement. As long as you can convey critical findings and corrective measures to a few people of varying technical levels, you'll be fine. Check out something like Toastmasters if you feel weak here.

Websites: A few of my favorites off the top of my head:
http://carnal0wnage.attackresearch.com/
http://www.irongeek.com/
http://g0tmi1k.blogspot.com/
http://www.securitytube.net/
https://www.corelan.be/
http://pentestmonkey.net/
http://www.room362.com/
http://www.pentestgeek.com/
http://www.darkoperator.com/
http://pauldotcom.com/

Paul from PDC publishes his list, if you want a quick way to jump-start your RSS collection: http://pauldotcom.com/PaulsFeeds.opml

Free Material: See above...

Get on Twitter as well, even if you don't participate. There's tons of interesting information getting tossed around regularly.

Well, I guess that wasn't so brief...

Hello ajohnson,

Thanks for the great reply and all the info. You have eased some of my fears about the OSCP. In regards to the other classes OS offers, I do plan on taking the OSWE and then the OSCE once I feel I'm ready. From all the research I have done, they diffidently seem like they are the best classes out there ATM.

About one of the books that you mentioned. Is Counterhack: Reloaded still relevant since it was written in 2005 or would something like the new hacking exposed be a better read?

and that's why I want to take it 

Thanks for coming out of lurker status and for the kind words for our community.

Be sure to check the pinned topics at the top of this board. Should give you plenty to start you off.

Keep learning, keep sharing,
Don