Rob, Are your CRM Activities making it to your Outlook calendar, but Outlook related items not updating CRM?
Your CRM Activities should sync up to Outlook if options are set-up right.
The easy way I was told was the CRM/Vegas idea "What happens in Outlook, stays in Outlook". If you create an Appointment/Task in Outlook, you need to use the Track in CRM function. Remember, this won't immediately update (minimum is every 15 minutes) unless you go to CRM > Synchronize with CRM; after this is done, you will see your Outlook created item on your CRM calendar.