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In the case of a normal weapon like a rapier or longbow being wielded by something humanoid, I'd add them as gear, because if you bootstrap them, if the PCs disarm him, and then he flees without being able to retrieve the weapon, you wouldn't be able to delete it.
I forget exactly how we have polymorphing set up in 5e. I know in Pathfinder, polymorphing into a non-humanoid form controls what equipment you're allowed to equip, and handles the rules for merging the equipment into your polymorphed form, but I don't remember if 5e has that same handling. So I'd add the weapons and then test what happens after the polymorph.
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