Just to follow up on this- I went to SoCal a week or so back, travelling with 4 watches in a travel case and one watch on my wrist.
Flying out to my destination was no problem. Coming home however, TSA did stop me in the security check and asked to inspect the contents of the travel case. They saw that it contained 4 watches, but still insisted on running it through the x-ray conveyor belt twice. After a small group of TSA folks stood around discussing something, they brought my watches back and let me on my way.
Not a huge deal in the end; minor inconvenience, but I can't help but feel that maybe I jynxed myself a little by posting this thread before leaving on our trip?