Here's an e-mail I received.

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I'm starting a dialogue with the TF team today to figure out what we need to make sure these get in game. Part of the problem with hat paintability has been a confusing process of migrating assets from our internal development snapshot of the game (called "staging") to the pre-release snapshot of the game (called "rel"). We also want to have a public set of tools in place so people can manage and subject changes to their assets that can go directly into updates with minimal oversight. That's probably a few months off, so we're looking into what we can do in the short term to get these hat visual changes in.