Cloning/backup software confusion?

Hey guys, I wasn't really sure where to put this, so I went with the applications area. I have a friend who goes away for months over the summer. He has a computer running vista where he goes for the summer. He has a PC running windows 7 at home and needs to take programs/data with him to the summer place to be able to use it there. He is NOT NOT NOT good with computers. Is there an easy way for me to set him up with the programs/data he needs for the summer? I was thinking cloning/backing up his hard drive on to an external he has, but I don't see any easy ways for him to get the programs/data onto the other computer because he is REALLY not computer savvy. Plus they are running different OS, so i'm a bit confused as to how to do this. I thought there may be some software application that may work for what he needs. Any help would be greatly appreciated.
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  1. Is cost a big issue?
    If not, my suggestion would be to simply enable remote desktop on his computer at home, set up the router to redirect incomming rdp to his computer, and simlpy have him use the software from his own pc.

    If you clone his system to usb, you need to replace drivers for it to work. The problem here obviously is, that you don't know what drivers the other computer needs unless you're there. And even then, you need to be rather skilled to install the right drivers - possibly using regedit from a windows dvd.

    use some remote administration software - like rdp
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