Hello MadCoder, and welcome to the forums!
xXxKrisxXx has accurately answered all your queries, I'm here to just give you some diversity
eLearnsecurity's PTP is I think a great course for someone beginning into the security field. I've done only this course, but based on the reviews of other courses, I guess PTP and courses from hackingdojo are the only beginner friendly courses out there.
Though PTP covers a lot of material (network, web and system security), it doesn't go too deep into any of it. But it does provide you a good security foundation so that you can easily dive into other courses like OSCP and SANS etc.
To get the best out of this course, use some outside references along with the course material. I used 3 books: The web application hacker's handbook, Counter Hack reloaded and The shellcoder's handbook to accompany each of the 3 course modules.
1.) Being on the Admin side for so long and not the black/white hat side, does these courses train is such a way that someone with my experience could understand and retain and not just throw out random how-to's.
I can't talk about experience as I don't have any (will be graduating in 2-3 months), but retaining requires a lot of practicing. Presently, the course has only a few labs but in late April they'll be providing lab environments which students can access into, and practice their skills. It might require 'purchasing' some lab time, though, nothing is finalized yet.
2.) My MCSE was was $8k. My MSTS was $6,500. My MCTIP was $10k. This entire course and cert is only $650? WOW. Why?
coz they aren't Microsoft