Hahaha, if you want to get really good, you should play CTF (Capture the Flag) competitions. They are kinda of like jeopardy style competitions where the difficulty of the challenge corresponds to the number of points you receive for it. The challenges will be across a wide variety of areas, but almost always include exploitation and reverse engineering. A good beginner continuous (no end) CTF is http://overthewire.org/wargames/. Other than that, read a lot of http://reddit.com/r/netsec. Netsec always has good writeups on real vulnerabilities and exploits. Stuff like assembly take a long time to get good with and practice makes perfect. I know some guys who do malware analysis and they can take apart polymorphic code like a first grade reading assignment only because they look at it all day everyday.
holy crap! Thanks! 
I'll definitely check this out. Too cool! 
And yes, assembly is tough. My original plan was to learn enough to make it not completely muddy when looking at disassembly which in itself also is very tough, but I gotta start somewhere. It's all very new right now but I get to work this mush in my skull again for the first time in what feels like years LOL.
Also, sidenote, I'm hoping that a better understanding as to what happens "closer the metal" will improve my optimization skills in C++ as well.
