|Try copying one of the symbols from Outlook into a Word doc and see what happens.|
For what it's worth, I just tried this:
I inserted a ≥ and a ≤ into a Word 2003 document using the method you mentioned above.
I then copied those symbols into Excel and used the CODE function to find their ASCII code.
They both returned a 63, which is the ASCII code for a question mark (?).
I then printed both the Word doc and the Excel doc and everything printed fine - I was able to print a ≥ and a ≤ from both applications, even though the ASCII code is incorrect.
I know this doesn't help, and I can't test this 2010, but I thought I'd point out the code difference just in case it points you in some direction.