Here I will detail some of the problems I ran into during migration from Android to WP8, and how you might recognize them/fix them or better yet, avoid them. Hindsight is 20/20, knowing what I know now, this is how I would go about things. The general gist is Cloud, then Outlook, then New Phone. I will refer to your current phone as Old Phone, and the Windows Phone 8 you are going to buy as New Phone. I'll refer to Outlook.com as OLDC. I am assuming you are coming from an existing smartphone (probably Android), that you don't use Exchange for email or calendar, but you do use Outlook on the desktop. You might currently have your Outlook calendar syncing to Google calendar.
A) Take care of the Cloud prerequisites. Before you even go to buy your Windows Phone, do the following, in order.
B) Take care of the Outlook prerequisites. This is all still before you buy your phone. Get your Outlook syncing to Hotmail correctly.
C) Now that you are ready, get the phone. Charge it up. Enter your Live ID, and let everything sync to the phone. Install some apps while this happens in the background. If you really liked Google Voice for your voicemail, there is an excellent app called Go Voice that is even better than the official Android Google Voice app IMO. Download it and configure it. Watch out for 2 factor auth here too. You will also want to add your LinkedIn, Facebook, and Google accounts on the phone.
If you have two factor authentication (SMS confirmations on all Google logins) turned on like I did, this applies to you. When you go to link your Google account from Hotmail/Outlook.com, make sure that you are LOGGED OUT of your Google account in the browser before you start the connection process. The linking process will not allow you to use the one-time passwords from Google, you have to use your "real" password and an SMS confirmation from your Old Phone. The problem is, if you are logged in to Google already, the connection wizard will seem to work without asking you for your username or password. Then your two factor authentication SMS will kick in, and it will send a text message to your Old Phone. But there is no form on the desktop browser's web page for you to type the SMS back in to, the wizard says you are done. So you'll wonder why you are getting the SMS code. This will happen over and over, about every half hour, SMS after SMS, until you go back in and delete the connection, log out of Google, and start the wizard up again. To avoid this:
Make sure you are logged out of Google. Start the connection process from Hotmail or Outlook.com to link to Google. You will now be prompted for your username and password. You will get the SMS authentication box on the next screen. Type in the SMS that was just sent to your Old Phone. Check the box to not be bothered again on this device. Click the button to continue and finish the wizard.
I now have this working. The key is to only use the new Calendar that was created with the Outlook Connector. I have turned off the views of my original calendar and put all events in the new Calendar that is seen on Outlook.com. So after copying events to the new calendar, deselect the check box to view the original outlook calendar.
I guess I missed this step in the Outlook Connector setup.
Now that this is working I am a happy camper. Love the Nokia 920.