1. Apple has removed sync services in OS X Mavericks. Therefore, you cannot sync Outlook 2011 with Contacts or Calendar.
2. Apple has removed the ability to sync through iTunes in OS X Mavericks, so that, even if you use Contacts and Calendar on the Mac, you can only sync them with your iPhone through iCloud, thus exposing all your contacts and calendar information to the mercies of the Web.
3. Microsoft does not not support CalDAV and CardDAV in Outlook, so there is no way to sync directly through iCloud, except perhaps by setting up a Microsoft Exchange account.
4. Apple makes it extremely difficult (virtually impossible) to revert to a version of OSX that is earlier than OS X Mavericks once Mavericks is installed.
In short, we are screwed and neither company seems to care.