I’m a control freak personally, I rarely use those software type of backups because I don’t trust them very much.
Besides, I’m the kind of guy that knows exactly where all my files are, and I havea standard procedure to backup to dvd manually everything I want.
Tips on successful file management :
1. Put all your work/business related files into “My Documents”. Do not scatter them outside. Same applies to music, videos, photos - keep them where they should be.
2. Keep a note that software settings (such as Illustrator pallette, or filetype settings that are customized for you) can be transferred via the Windows Files and Settings Transfer wizard. Use that and save just all application settings.
3. As for Outlook, you can simply copy the entire Microsoft Outlook data file, which contains all your mail account, calendar, contact, memo, task related infos as well as all emails/attachments. No need to export/import anything, just copy the whole damn datafile. Outlook.pst is the usual name, and if you have lots of data you may see archive.pst as well.