Thanks for the responses!
I'm looking into expanding my student license right now (thanks for that, perfect timing).
It seems I'll look into the different plugins for Maya since that might be the least expensive option for me (and sticking with Maya is probably more beneficial for getting a job). I've heard that Maya is considered the standard software for animation several times before, and as far as the animation itself goes, it isn't too bad (there aren't many "intelligent" features, but if the rig is good the animation is pretty straight-forward with lots of curve and time control). I've never been a fan of the disjointed processes in Maya for rigging, setting up controls, painting weights and other information, and the lack of real-time, smooth feedback. For a piece of software with so many iterations it doesn't feel very advanced (or refined).
Messiah seemed promising with it's fast rigging and intelligent weighting, but plugins may be the realistic answer to streamlining the rigging and animation process for me as of now.
Thanks 
Maya 2011 added some new skinning tools (largely adopted from Max, I think), which are envelopes, instead of just weights. But don't let the Messiah videos make you think it's . You still need to paint or adjust vertex weighting by hand, to some degree or another. It's just one of those processes that requires custom work/weighting. You have to go in and handle trouble spots like armpits, shoulders, elbows, knees, etc...with care.
Maya 2011 supposedly has enhanced viewport performance, so playback should be improved. I remember taking a Character Animation class using Maya, and it was fairly good. I still prefer CAT in 3ds MAx because it is really fast and easy to set up, as well as having some great animation tools (CAT Motion to name one)...but it currently has some critical bugs that Autdesk has yet to fix. I'm hoping that will get done when 2012 gets released in a few months.
Still, Maya would be good to stick with if you plan to seek employment in that area.