I'm not 100% sure how Microsoft does it, but I can give you an example of how Yahoo and AOL work. For Yahoo, once the account is deleted for whatever reason you can recreate the same exact name again. So you could basically do exactly what you want to if it were Yahoo. AOL is a little different in the way they handle old deleted/cancelled accounts. I've heard that they do dumps occasionally and release names to be recreated, although I can't confirm this. If they work it like AOL though you could check an email that's been dead for whatever reason for years now, and you still can't recreate it.
So basically if they do it like Yahoo, then you should be ok and able to do it. If they do it like AOL, you're pretty much screwed unless you can reset the accounts and gain access to them that way. I'm not sure of any bots that will do this exactly for you, but I don't see why you couldn't get ubot, or zennoposter to accomplish this as mentioned above.
