Global css files have caused me headaches before. CSS usually isn't namespaced, so if two different modules create a div with a class of "box", then the intent of one overwrites the other. Also, styles on the [a] tag, [p] tag and other basic tags (ie. styles not based on classes or id's) will wreck havoc on 3rd party controls as your global style sheet cascades onto an html component that was designed assuming no other css on the page. Inappropriate usage of text centering to center elements can lead to hard to debug global centering. So I favor multiple css files. I've seen css managers (http modules that merge css together at request time), but decided the extra http requests is well worth limiting the scope of the damage ill considered css can do to my application.
