This is Outlook 2011 for Mac running on a Powerbook Pro i7 Retina 

Outlook is version 14.5.7

Mac OSX is 10.11 El Capitan

Itunes is running and up to date

It appears that contacts and calendar from "on my computer" are not syncing.

As i understand this, Sync Services is responsible for copying these items from Outlook to Calendar and Contacts?

Sync Services is running. I have reset it, and replaced all of the .plist preference files. I have ensured that my Sync Servers settings in Outlook are on and functioning.

I have monitored Sync Services using the Activity Monitor and see that when I make additions to the Outlook Calendar on the "on my computer" side there is increases activity on Sync Services as shown on Activity Monitor. I also see files updating in the Application Support/Calendar folder. I'm guessing these are resulting from my changes and Sync Services.

I also have an Exchange Server and I can place calendar items into my calendar on the Exchange calendar and they will update to the Mac Calendar application and show up on my iPhone. I cannot state that this is a result of Exchange, Sync Services, or iTunes. I can only say that it works.

I have cleared all of the calendar files by shutting down calendar items on each accounts setup in systems preference "Internet Accounts" - doing a Safe Boot and then restarting everything. I verified that all accounts disappeared in Calendar after I did this and were re-established when I reset the Calendar setting in Internet Accounts.

I ran Cocktail to verify permissions and clear all cache files for system and applications.

I have rebuilt the Outlook database using the utility.

I have rebuilt Spotlight.

I have read and implemented most everything i can find dating back for the last two years on various boards around the internet for this topic.

Naturally I'm open to ideas at this point and ready to redo anything that I may have missed.

My conclusion right now is that something didn't get fixed in Sync Services when El Capitan came out. Outlook was having trouble syncing - with Exchange is the theory - but Outlook tries to sync with a lot of things when it first starts up and so it might have been that syncing with El Capitan Calendar and Contacts was the actual problem which got disabled in V10.5.6 - that is the update that "fixed" the well-publicized hanging issue with Outlook and El Capitan. But then immediately comes 10.5.7 with nothing in the description that alludes to any relationship to the syncing issues. So clearly I have little or no real information and just some conjecture that says perhaps syncing from Outlook to Calendar and Contacts isn't working because of Sync Services.

BTW - can anyone confirm whose product is Sync Services? is it Apple or MS?