Can sync calendar or send mail but not both

In order for my calendar in Outlook 2007 to pick up appointments entered on my iphone, the icloud outlook ad-in must be active. However, when it is active, any email I attempt to send just sits in the sent mail folder, showing "date: none", and the sender subject line in bold, not italic. When I uncheck the icloud ad-in, emails send, but of course, the calendar fails to sync.

Thanks for the suggestion; I will study this carefully and see if I can figure out a permanent solution. I've been to slipstream before; it's not exactly syncing for dummies. But perhaps with my additional experience I will be able to find the solution I'm looking for.