OSCP of course  The PWB course doesn't go directly into debugging, afaik. In fact it's mostly based around penetration testing with backtrack 

Learning the tools, from recon to exploitation and post-exploitation, and also not using the (common) tools, but also using alternative tools like Netcat (the swiss army bla bla  )

What OSCP and OSCE really takes, is primarily a lot of dedication and the ability to learn. Secondary, being able to think out of the box and think abstract yet logic. (That's what it takes of non-technical skills, but the ability to learn technical information is of course a must.)

Anyway, that's just my opinion and I know people are different too. Some might learn better in a class environment and therefore Hacking Dojo, may be better, but if you can do most on your own, then OSCP is the way to go. Even if you should get lost, there's help to get on the #offsec irc channel even though occasionally the help may be vague, not because people don't want to help, but either because you're making it too hard for yourself or because it's expected you find out by yourself because it's one of the ultimate ways to learn, you'll probably remember it the rest of your life if you do so.

For example, can you remember everything you learned during school, education, your job etc. down to almost any detail? Now compare that with what you taught yourself, by e.g. self-study, who knows it better? 

Anyway, I'm sure there's someone else that wants to help you in the right direction as well.

Cool

I think I'll continue learning python and bash over the next few months, then somehow build up the courage again and speak to my manager about enrolling in the course

I'm not nervous about his reaction because he said he will support me, but the fact that its alot of money, and technically it won't help me to do my job any better, as we're a standard Microsoft house

I think maybe around May/June time I will ask, hopefully by then I will be confident with python and bash

Cheers

I'm fairly fluent in VB.net but obviously its Windows only, and I'm trying to get rid of it from my memory lol

But I'm pretty much going through the free online Google class on python, only watched part 1 so far, but I am hoping it will at least make me more familiar so I can begin to code my own small programs etc

Hopefully once I get better, I will be able to code my own aircrack-ng so I can begin to go into leap/peap/radius networks but that is later