This is not what you want to see when you load up iTunes on both computers once the files have been synced.

Thank the lord for the plethora of backup files that WL Sync makes every time it syncs iTunes. I managed to load up the last one from earlier in the evening and it was all ok. But If I hadn’t have found that file, I would have to import every song I own again, manually.

So, as of this day, screw Windows Live Sync, hello Allway Sync. http://allwaysync.com/

It seems to work well, a traditional LAN based sync service. Very nice as I can plug in my work backup USB stick and it will auto sync to it. There is much more to it and will probably review it once I’ve got it set up.