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You lose the benefits of style caching with inline or dynamically applied styles, and inlining makes each HTML payload larger. Also, applying virtually all of your styles with JavaScript, after the DOM has already finished loading, wastes CPU cycles and just feels like going against the grain of CSS to me. You make a few arguable gains with this technique, but I feel it might be throwing the baby out with the bathwater.

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The payload probably won't increase as much as we'd think thanks to gzip, and you can apply the styles via server-side rendering rather than waiting for the JS to load.

We also need to consider the time from request to a ready page: if you're on an incredibly slow connection, then having the styles immediately rather than waiting on a second round-trip is a huge win. I agree that there are pros and cons, but some of the pros are actually in performance; it's not immediately clear which technique is more performant overall in what contexts.

You can get around this by using compilation tools, just like Compass does.

So, create a problem, and then solve it?

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