That's almost the same setup that we have (Postfix, Cyrus IMAP, Squirrelmail, authenticate against external LDAP).
The migration is pretty painless. Just configure Zimbra to authenticate against external LDAP. Then use imapsync to migrate the messages from one server to the other. Then use CSV or LDIF export of the addresses books, and import them into Zimbra.
If you know perl (or are good with sh, awk, sed, and so on), you can automate a lot of it using scripts.
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Freddie
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