Hello Martin,
After I posted to the group, I found that it has to do with Tkinter exclusively. When I switched to using PyGTK for my GUI it would compile with no problems and worked for the single .exe. I managed to figure this out by screenshoting the console window quickly before it closed and it wasn't loading the MS Visual Studio files correctly.
It was giving me a weird import hook error (attached the screen shot) and after Googling a ton more, tracked it down to someone else mentioning that it wasn't importing an archive correctly. Since pyinstaller worked fine on python scripts before adding in a GUI, Tkinter was my culprit. I don't know why it wasn't loading in the required files, and am really just too tired to work on it anymore. I spent nearly 4 days solid the week I posted this question trying to get it too work.
Thanks for finally approving my question though, you have a solid product and I'm glad it's around. I just wish it worked better at packaging Tkinter and gave a more helpful error notice.
Matthew