Outlook.com Switch

So I want to make the switch to Outlook.com. I really like where Microsoft is going with their services, hardware and overall strategy of unification. The problem I have, is that for years, Microsoft didn't have it together, so I've built up a Microsoft account based around my Gmail. Currently I have my Xbox, Skydrive and Windows Phone settings, purchases and information all stored with a Gmail account.

I know that I can migrate an Xbox from on Microsoft account to another, that's not a problem, but what about the purchases I've made in Windows 8, Windows Phone and my 25GB of Skydrive space I got for being an original user? Can I migrate those settings and features to a new Microsoft account, I'll take a one time only, no take backs approach if that's all Microsoft wants to give me.

I really like what Microsoft is doing and want to support them, but I don't want to have to throw away the digital history I've built on another account in the meantime.

The ironic part of all of this is that I want to use Microsoft's services now, but because they were so lackluster in the past, I didn't and now I can't use them because of the features I've built up on those other accounts. Has anyone else been able to successfully navigate the migration of Microsoft accounts to resolve these issues?