Now that's a question to spark debate!

Without leaning one way or another there are a number of different
approaches you might try.

Have you considered CSS frameworks such as Blueprint CSS[1] or the 960
grid system[2]? These approaches help to standardize your CSS by
providing the basic page layout with cross-browser compatible, minimal
and semantic markup. You are then left to style (bring life to) the
page with the content and look and feel.

There is also the old-school developer approach where you get a little
more freedom. You start by resetting your css [3], then set all of
your basic styles and general classes (which probably differ little
across sites) and set your site/section/page/page sub-section specific
styles. Traditional developers like this approach because they use
their own naming conventions, and often can re-use the base css files.

> I'm guessing this sort of structuring comes at a cost because a number of
> requests need to be made to the server.

You're certainly right with the cost in terms speed, by increasing the
number of CSS files, but what about the cost of development time,
readability and re-usability?

-- 
Matt Fellows
http://www.onegeek.com.au/

References:
[1] - http://code.google.com/p/blueprintcss/
[2] - http://960.gs/
[3] - http://meyerweb.com/eric/thoughts/2007/05/01/reset-reloaded/


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