Well to my knowledge Android can sync with Outlook... Using Exchange. Are you not using Exchange...? I use GMail so the integration is seamless on WinMo and Android, I don't even want to look at Outlook if I can help it
Also, if you have a rooted device you can use the wifi router w/o VZW knowing - to my knowledge. Much in the same way that you've done so on your WinMo phone... VZW probably doesn't want you to use your phone as a wifi router, and since the TP never 'officially' supported the feature, you can fly under the radar.