I'm running an Mac OS X Server (10.6.7) with iCal, Address Book and Mail enabled. My issue is that the clients (iCal and Calendar in iOS) keeps asking for passwords on strange intervals, and it usually results in it not accepting the right password until you restart the client. It can run smoothly for days and some times it just goes completely bananas. It makes no difference if its a regular user or a Open Directory user.
This happens to all the services mentioned above but iCal is the worst.