Thanks to everyone for the help. However there seemed to be an issue with the fonts not being "compiled" for our flavor of windows/pro. We ended up getting the 64 bit font compiler, setting some env variables, and then tweaking the the font's .src files to modify our existing font. Kind of a process: tweak the font's .src file, compile it to the .fnt file, move it to the correct spot, view it in Pro, get feedback, tweak the font, compile it, move it, view it, etc. The PTC website had some helpful info on this one. Nothing says fun afternoon more than 4 engineers trying to decide how long the slash in a zero should be.
Thanks again.