i doubt the TSA is concerned about how many watches you're carrying as much as they are about the amount of fluids in your toiletry pouch
in my personal experience i routinely carry 4-6 reps in my media backpack with my notebook, camera, device chargers, etc and no one cares a tiny bit
this kinda stuff serves to reaffirm the fact that we have only one life and only a few of us know how to live it
props, congrats and thanks ... not to mention the heartiest best of wishes