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Ben
Take a look at the most downloaded files on www.download.com, www.sourceforge.net or similar. Sourceforge.net has lots of useful software but its most downloaded list only has the file/program name shown - there isn't any short description - so its not very user friendly.
Install all the installation packages on the harddisk, preferably on a seperate partition, or burn them on CD. If his system crashes and he needs to reinstall some software, downloading via internet of multi-megabyte packages via a dial-up line might not be an option.