in reply to How to maximise the content of my data CD

Sounds like homework to me ...

You could always use an archiving tool to compress all of the files and span them to the desired media size. I brushed off a version of pkzipc (on windows) and had a play. The following command compresses the data and creates a number of 700Mb files suitable for dropping onto CD.
pkzipc -add -span=1.44 *.doc

Similar opportunities exist with tar on UNIX systems.