Recovery Of Information From XP To 2007?

My boss had me upgrade a co-worker's home computer from Windows XP to 2007. I made the mistake of not doing a clean backup of all the documents and other information.eedless to say, the upgrade wiped away all the software and the setup from before. Working with the co-worker, most of the programs have been restored, but there are two issues that right now are the most pressing, which concern Microsoft Outlook and Itunes.The co-worker had a series of older e-mails and contacts saved in Outlook that are obviously no longer there after the upgradeAs far as ITunes, there is a folder for MyMusic but only what appears to be one large file document for the music. What confused me in this instance was that there were 3 songs that were not recently downloaded in that folder. If the co-worker plugs in his Ipod to charge it, will he lose the tracks there? I advised him to contact Apple to look into his account and recover any songs that he downloaded.