Moving from Windows Phone 8 to Android. Outlook --> Google Cal

I've been a Windows Phone user since launch day of the Samsung Focus. All of my contacts and calendar appointments are in Outlook/Windows Calendar because of work (I'm a teacher). So, I'm don't know how hard it would be to move my contacts and cal over to Google and am I going to have any problems with that?. At the same time, I need to be able to add info to my Outlook and it show up in Google cal on the Android phone I will get. Is this possible?

The bigger issue is the phone. I want a Nexus 5, but $399 is a lot on a teacher's salary. I also like the Moto X, but that's still $350, so the Moto G seems like a good deal at $200, but the Nokia 920 has Qi charging which is so great and the charging plate would probably work with the Nexus 5. NFC and 4G on AT&T would also be nice, too.

Last questions: Is it going to be a problem if I take the sim card out of the 920 and put it into the Moto X, G or Nexus 5? If I put a contact in Google contacts, will it transfer to my phone through the cloud or whatever?