Can not get MS Outlook to sync with Cal or iTunes. Worked fine prior to the upgrade to 10.9.3

Question

I want Outlook to be the primary calendar that I use to scheduling. Prior to upgrading to 10.9.3 this worked fine. I have tried every thing I know to get it work, Cold boots each app., turning off sync services on Outlook and restarting. Nothing I know works

Answer 1

What version of  OS X were you running before upgrading to Mavericks?
Sync Basics
CalDAV & CardDAV are protocols used by Apple, Google, Yahoo and others to sync contacts and calendars. Neither Entourage 2008 nor Outlook 2011 support CalDAV or CardDAV.
You can no longer sync Outlook with an iPhone or iPad via iTunes. You can only sync with an iPhone or iPad via a cloud-based service like iCloud or Google.
You can no longer sync Outlook local calendars with OS X Calendar (formerly iCal). You can, however, continue to sync calendars hosted on a cloud-based service like iCloud or Google with Apple's Calendar.
You can no longer sync with any third-party apps running on your Mac that use Sync Services, like Entourage or Outlook.
If you want to stick with Outlook, I suggest you look at Office 365. Otherwise, moving to Apple Mail, Contacts and Calendar with iCloud might be a better option for you.
Until Microsoft adds CalDAV and CardDAV support to Outlook, there is no way to sync other than get an Exchange account. It's $4/month Exchange Online.
http://office.microsoft.com/en-us/exchange/microsoft-exchange-online-email-for-b usiness-FX103739072.aspx
UPDATE OS X
You mentioned you were running 10.9.3, you need to upgrade to the latest version of Mavericks.
OS X Mavericks 10.9.4 Update (Combo)
http://support.apple.com/kb/DL1755
Post Date: Jun 30, 2014
File Size: 958.2 MB