So I tried everything except for the scanpst. When I thought about it again it didn't make sense because I tried a different profile without loading the PST and it still errored out.

In the end I checked the event viewer application logs and it pointed to the outllib.dll file that was causing it to crash. I C$ shared to a different machine and grabbed the file, renamed the old one and dropped it in the C:\Program Files\Microsoft Office\OFFICE11 directory.

We opened up outlook and went into his calendar and it opened like it should. Problem solved.