The problem here might be that implementing this would mean going back through thousands of previously released hats and flagging them all with target folders to appear in. It would take some one a couple weeks just to go through them all...
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although this is true, from experience on other servers, most holidays have a certain file extension for the file, i.e. classic_vday16, classic_xmas16, classic_easter16 - which may make it easier to categorise them