Here are two quick quirks of Microsoft’s File Transfer Wizard:
1) The software is very sensitive to which version was used to create and restore the files, and does not appear to be forward or backwards compatible. There is a workaround by using the USMT command line tool if necessary. But the best way is to use the Microsoft Windows CD to both create and restore the image.
2) The file transfer wizard does move the contents of the Local Settings portion, which includes your Outlook PST file, probably the most likely item you’ll want to transfer.