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I’d go with one file, because you have to factor in what’s convenient for you. Trying to juggle multiple files eventually becomes more trouble than it’s worth. I tried it and hated it.

The only time I’d really justify having a separate file is if I knew it would only need to be served to one set of users, like a style.css for everybody, and a account.css for logged in users (which still piggybacks on style.css for the main styles) to style their account areas. And even for that, I’d cringe when doing it.

One file, minified, gzipped = easier to manage, less requests.