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Some options give proficiency with an entire group of weapons instead of, say, "Simple Ranged" or just one specific item. For example, the Dwarven Weapon Proficiency feat gives training with all axes and hammers.
Perhaps the proficiency selection pop-up could include a section at the end for picking weapon groups. It would override the check-boxes for anything applicable, like how the "Simple Melee" selection auto-picks everything below it.