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Can anyone give me any tips?
Word files can be saved in HTML, although I've heard the results are fairly... well... questionable. Generating from a plain text file would be quite straightforward in Perl or PHP, depending on how much formatting you'd need. You'd basically set up a page template in plain HTML, serve it using Perl, and then insert your text at the appropriate point.
This could also be done using SSI (server side includes) if you've got it enabled using the <!--#include file="filename.html" --> instruction to include the contents of filename.html at that specific point in the HTML
Generating the links is a bit more tricky, but can be done with Perl's readdir command to scan the contents of a directory - if you put all your documents in this directory, you can create a set of links to whatever happens to be there when the script is run.
If any of these sound like the kind of thing you're after, shout and I'll do a code snippit.