Ok I figured it out. I'm not exactly sure what the b or break command
within pdb does but it doesn't seem to work in some instances as I
described in my initial post. Does anyone know what the constraints
are to using the break command within pdb?
What does work is to import pdb in the file you want to debug and then
place the command pdb.set_trace() where you want to start debugging.
This is an excellent quick tutorial for anyone who is interested:
http://www.ferg.org/papers/debugging_in_python.html
It explains the commands bit better than the pdb docs do. I had
actually found this site about a week ago and completely forgot about
it.