Well I want as little as possible involved here to ensure any connection issues that arise are on the POP3 server end, which is why I wanted to use telnet in a script somehow.
I'll look into Python though.
[EDIT] It was easy to get this done:
Code:
import getpass, poplib
M = poplib.POP3('mail.server.com')
M.user('email')
M.pass_('blah')
numMessages = len(M.list()[1])
print numMessages
Now I just need to figure out how to write the output to a file if something wrong happens.