I do most of my flying between the same two airports (BNA and LAX, before that, BNA and MSP or SEA) all the time, so I don't see a wide variety of WTMD settings, but I never have a problem with my belt buckle, watch, or rings setting them off; my phone (BlackBerry) and keys will always do it. I have yet to see a woman get wanded for an underwire who wasn't already in secondary for some other reason.

Key to avoiding problems with security is to be boring. Pack boring stuff, act boring, don't get excited about anything, and be efficient. If you forget and leave your "freedom baggie" in your bag and it causes problems, just own up to having forgotten and let them put your bag through again. I would suggest packing your keys and phone into your carryon/purse as soon as you are done with them, so you don't have to dig them out at the checkpoint and put them in the bin. Wear slip-on shoes, so you can get them off and on quickly.

My basic strategy at TSA checkpoints has been to act as nonchalant and easygoing as possible and to get through quickly, without making a fuss about whether I have bottles that are over the limit by .1 ounce or whether I am risking gangrene by going through barefoot or in stocking feet...I just keep my eye on my stuff and act as cooperative as possible, so that I can get through and forget the TSA is even there, and they can forget about me. Of course, when someone does manage to get something past them, it will be a boring, nonchalant guy like me who's done it a thousand times, not someone who's being confrontational.