hey mackwage,
welcome to the forums. I'm not too sure if the v2 examination differs between the v3 examination but I'd imagine it would. To answer your first question:
1. How far do you personally think one should be able to penetrate the thinc.local network before being comfortable with the cert test? Like I said, I understand it's a very subjective question but you take on information in the labs and exploits performed in the thinc.local network versus the cert test would help great.
A similar question was asked on the offsec forums which you should have access to, and a summarized answer to it was that they suggest penetrating a minimum of the all of the machines in the student network disregarding some of the harder machines. The link to this thread can be found
here.
My personal opinion on this is I think you should penetrate every machine you can in order to help prep you for the exam. I personally wasn't able to hit every machine on the student network but I did get access to all 4 subnets and hit a few machines on them too. Every successful penetration into any lab machine makes you feel more ready for the exam.
2. What outside resources have you used to further development your learning of the content? Specifically do you have any great links to sites that you found particularly informative or helpful on the different topics? I have done TONS of Google searching and found some useful sites but a LOT of outdated ones as well.
I had posted my review of Pentesting With BackTrack on my site (but it's currently down right now), you may want to check out this link in a couple of days ->
My PWB v3 Experience. I still have access to the resources that helped me out throughout the entire course so hopefully these will help you out:
http://carnal0wnage.blogspot.com/http://www.exploit-db.com/http://securityfocus.comhttp://ethicalhacker.nethttp://www.offensive-security.com/metasploit-unleashed/http://irongeek.comhttp://securitytube.net/http://www.packetstormsecurity.org/http://www.securityaegis.com/http://synjunkie.blogspot.com/http://www.corelan.be:8800/Milw0rm was up at the time and it helped out too - but the sites gone now. That's okay though because exploit-db's taken over the project. There's a few active OSCP's on this forum so don't hesitate to ask other questions, were here to help! Good luck on your adventure in the course, I had tons of fun!
-kris