cpayne,
For this PITA file just take one read of the attached file before going to bed and then
apply the verbage to the attached Lcam.

I have seen this kind of problem when trying to do a pocket. When it dosen't work, which can be due to a whole
bunch of things, the drawing, the tool, practical machining approach, corrupted file. Sometimes it's just better to take a different approach and it will get pocketed. BTW, i tried to pocket it with a different program and it was even worse. You won't pocket something if you can't create an offset for the profile. So that is always my 2nd option after a check of the drawing.
Please note that i wanted to do this using an 1/8" end mill. with smaller cutters it probably would have been easier i guess.
RICH