First hurdle, trying to get my contacts into Windows Live and keep them synced. I have a Windows 7 VM, installed all the Live pieces, Zune, and MobileMe. MobileMe lets me sync to Windows Contacts (the equivalent of Address Book on a Mac). And I have a Windows Live Mail program that also shows Calendars and Contacts. But the contacts there are from when I used MSN Messenger in the past, and aren't my Windows Contacts.

Also, it looks like I managed to blow up my MSN contact list somehow. I saw people online, made a change to use my miniinfo.net e-mail instead of the 11 year dead e-mail address I had previously. Everyone is in my list still, but no one is online now. Every time I try a new mobile OS, I blow up IM stuff, as something similar happened to Google Talk. *sigh*