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Digester late to this discussion. Therefore random thoughts.
Regarding UNIX--ignore at your peril. Your server may be NT today but could
be UNIX next week. Do you want to have to rename all your files when that
happens? Biggest problem I see with (most, I guess) UNIX is not with
filename length but rather with use of mixed case in filenames. NT ignores,
but this is important to UNIX. Suggest all lower case.
While "chapter" may be a valid concept, "page number" is not on the internet
or on an intranet. Think ahead and assume the web is where your document
will be someday if it isn't already.
My suggestion is to name the graphic to describe what it is and not where it
is used. If your document will never (?) change, "figure4-3.gif" is then
fine, because in one sense that's what it is. Since the writer that follows
you will learn your document and your "convention" from scratch anyway, I
wouldn't worry too much about conventions.
Image1.gif, image2.gif, etc. is what you get when you save a Word document
as html. What else could they do? Assume you have to change the names.