A Guide to becoming @outlook
With the introduction of outlook.com,
like with the introduction of live.com, many people are wondering and jumping at the ability to get their new address running. There are a few ways to do so, but only one way to have a complete transition. These are all from my personal experience. If you're a Windows Phone user, this involves resetting your phone to default settings. Doing this will remove all of your apps, including games, their saves, and all of your app data. If resetting your Windows Phone is not a problem you're ready to go.
The first thing you'll want to do
is head over to outlook.com. Go ahead and sign in with your current email address associated with your Microsoft Account/Windows Live ID. You're be greeted with the new outlook webpage. In the top right corner is a cog for settings. Clicking on it > more mail settings will bring you to advanced settings. Under Managing your account is an option to Rename your email address.
Why rename your address? When you rename your email address, your new ID works just like your old one. Your new mail will go to your inbox, and you can choose to keep your old mail in a separate folder. All of your other Microsoft account info - like contacts, photos and Office docs on SkyDrive - will also switch to your new address within a few days.
Type in the name you wish to use.
Be careful as there is no way to know before hand if the address is available (don't type buttface expecting it not to take) and I do not know if this process is repeatable. From there you'll be asked to confirm and given an option for older mail to go into a new folder or continue to filter into your inbox. Your previous rules for your inbox will transfer over. A tip: you can have them sent to a new folder so you know who/what needs an updated email. After pressing okay there's no going back! I should mention if you created an alias, it is possible to delete the alias to free up your desired account address. The process to free up an alias seems to be a few hours. I read a recommendation to do so the night before so it'll be available in the morning. Always be aware it might be taken. Thank you, internet.
Everything should begin trickling down
...from this point on. You'll notice some quirky sign ins on your Windows 8 machine, your Xbox will probably ask for your password again, all of which is normal. The first thing I did was make sure my Desktop (running Windows 8) was good to go. Sign out and sign in should be enough to show that your address has been updated. The Windows Communication Suite should also ask for an updated password/address but will work as expected after that.
Next, check your Xbox
If you have one, be sure it has adjusted. These changes will take time. Going into Settings > Account Settings > Account Security > Change my Windows Live ID will show you what ID it is currently using. *You don't need to change this manually.* It took me about 3 hours before it changed to my new address. I didn't wait for my Xbox to do this, so it's up to you if you want to. For those with Facebook, I changed my primary email address to match my new address. Easy peasy.
Now for the painful part
If you're a Windows phone user go through your phone and back up your pictures, videos, and music using Zune. Are you ready? Go into Settings > About > reset your phone. Close your eyes and wave good bye to your old data. At least now you'll be able to play those games over again in a legit manner. Your phone will reset and ask you for your Windows Live ID. Put in your new information. Now that your phone is reset, I recommend going to windowsphone.com and click on My Phone > Account. This will show you a list (in pages) of all the apps you've purchased/downloaded. You can reinstall them all here one at a time. I CTRL+Clicked on each one to open them in a new tab and queued them up. Your phone will download and install them, just close the tab when it says Congratulations! Your phone will soon be back to normal as you fix your settings and pin your apps the way you want it. Resync your pictures, music, and video and be on your way.
One more service to talk about:
Windows Live Messenger will be frozen during this process. Your friends will appear offline to you and they will not be able to send messages to you. This has to do with the way (I assume) Microsoft handles the relationships in messenger. Your friends are connected through Microsoft Account. Simply changing an email address will not affect this. When a friend accesses your profile through the people web app, they'll be able to see if your old email is still associated as a Microsoft Account. Eventually this will change which will sync with them and finally you'll be able to see each other again.
A note for Office Outlook users
Using the Hotmail Connect Add-on: You may get an error with syncing. For me, this had to do with contacts not syncing. The solution for me was to go to the local storage of Outlook and remove it to start over. Close Outlook and navigate to C:\\Users\*username*\AppData\Local\Microsoft\Outlook. Create a New Folder and move everything here into that folder for backup purposes. Now open Outlook and sign in with your new account name. Everything should begin populating without error.
Following these steps
will result in a transfer to your new email address without compromise... unless you have a windows phone... Your last step will be to go through your services and websites you use and swap your email address. It might also be nice to email your contacts about the change. However, you will still receive emails from them in the folder you chose earlier. So screw them. Enjoy your portion of Microsoft re-imagination! Sound off in comments if you have questions or further advice~