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Nice post. With expanded use of css3 features (gradients, shadows etc...) this will probably become more of an issue, but I hadn't really considered the impact that compile to css languages are having.

With the dynamic nature of the DOM, it's going to be very difficult to automagically improve selectors (that x% unused figure only accounts for the current users actions, not potential actions)

Have to click a button for a single line of text? No thanks.
Anyone know the mechanics of what's involved with auditing and graphing CSS sizes with Graphite? What's instrumented and when is it logged?