Scott, just to throw this out there - if you ever decide to try the commercial route, and want to borrow some of the training materials I bought awhile back for MasterCAM, let me know. It is one of the main commercial packages out there, and while pretty pricey it is really quite good. It took me awhile to learn but it'll do just about anything. While it's often used in industry with Fadal, Heidenhain, and other fancy controls there are post-processors ('posts') available for Mach3 and I believe also LinuxCNC so it's good for hobbyist machines too. Since you're at Mizzou you can contact them for academic pricing also.
There are some other commercial CAM packages out there that are pretty decent. BobCAD/CAM is one of the more popular ones, a little cheaper than MasterCAM with a pretty huge academic discount. For free, you can get CamBam which is 2.5D for router-type machines and a lot of people seem to like it.
None of this is to downplay the hard work that Brad and others have put in on the open-source options. I personally am not ready to use any of the open-source stuff but it's improving all the time.