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1) If I upload them to the server, will visitors whose browser has cached the CSS file continue to use the cached version?
2) If so, what determines when their browser re-requests the CSS?
3) If I also uploaded all my HTML files, would this cause a browser to re-request the CSS?
When you need to change them, change their names. If you can't change their names, then set a short Expires header (like 30 minutes) for them via your server controls before you start developing changes. By the time you're ready to upload changes, most cached copies will have expired or will be set to expire shortly.
Realistically, it won't hurt to have them expire after a few hours as a normal practice. Shorter than that means more re-fetches, and longer than that means more likelihood of being stale if you change them often. It's all a trade-off.
We've got two threads going now... I posted a couple of useful links over here: [webmasterworld.com...]
True, but intervening caches may check Expires and provide the file locally. In the absence of a "strong" cache policy in the file header, the browser may get an old copy. The caching tutorial cited in the other thread [webmasterworld.com] covers this.