About a year ago I tried to get Syncing to work on Outlook 2011 because I really like it.  I like the look Calendar and I like the way the it creates different Calendars (with colours) for each catagory on my iPhone.

What I don't like is the way my Addresses in Outlook are duplicated, erased, added to randomly etc in Outlook.  It makes it useless.  

Since it was the holiday season, I decided to spend on day on this.  I even exported an OLM fine for back up.  That didn't work because I got a message saying that I quit the restore, which I didn't.  So I deleted my 2011 identity and went back to Entourage which works fine.

Then I thought that since I don't really care if Outlook syncs to the Apple Contacts or iCloud (which it does flawlessly), can I just use iTunes and ignore the syncing stuff?  Who knows, I might just try it again.

When I send a message to a "Contact Group" it only goes to the first person listed in the group emails. This is pathetic AND dangerous as I thought a message went out as it used to until I checked one day and NOOOOO. FIX IT QUICK PLEASE.
How do I add or delete contacts from my group(s) contacts? It looks like you have changed the system and not told us what to do for this!
In Outlook for Mac 2011, can one convert Smart Addresses to show the complete email address in headings; and can one convert the new heading to the old "From:/To:/Subject:" format?

I am having a hard time explaining this, but when I am trying to compose a message, I would type the first few letters of a person's name and outlook would autocomplete it. That's not happening anymore and I can't figure out why. 

Any help is appreciated. 

For example, I used to want to send an email to Joe Alstat and in the "To" field I would start typing "Joe" and it would autocomplete for me the rest of the name. 

Thanks for your help.
I have a new top of the line MacBook Pro.  I loaded Office.  The Outlook Autofill function does not work for email.  This is one of the most important things you do on a computer - fast access to email addresses without having to type in the whole address and getting address wrong, etc.  There is no dialogue box popping up telling me it does not work, there is no instruction as to what to do so I re-loaded Office three times, that did not work, so I stripped my SSD drive clean and reloaded my Mac OS and all my docs and Office.  How the %^%%$ do I fix this.