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You just add users to the system in the usual way AFAIK - adduser. I'm not sure if the UW IMAP server support support virtual users (users that exist in the mail system but not on the host operating system).
Root isn't allowed to do lots of things by default like ftp into a server and I'd be very surprised if you could connect to the IMAP server as root either. It would have the potential to give you big security problems. Have you tried as a normal user?
Your logs are typically in /var/log have a look to see if they give you any hints. My experience of UW IMAP is thats its just worked. The only thing I can think of is that the IMAP server is trying to use a secure connection and your client isn't. Which mail client are you using?
I think that for SquirellMail to use IMAP you need to have PHP built with OpenSSL support too, when I last build PHP I can remember playing about with this. Try connecting with something like pine (or even Outlook!) and see what they report.