Well, we did it. The trip went pretty well. They made me take off everything going through security (as I knew they would), but I was prepared. I had the OTSBH in my bag so that I didn't have to re-wrap. This meant that I had the wrap on when I was carrying a ton of luggage, but didn't have to chase a toddler and re-wrap at the same time.
I had considered just wearing it over a tank and claiming it as part of my clothing, but we were going to Anchorage and I packed my coat so that I didn't have to carry it. And, I knew it would take a while because they always insist on going through my diaper bag. It seems that no TSA employee has ever seen a cloth diaper before. And, the snaps on my nursing bra set of the detector. Yup, I'm gonna overpower a flight crew with a spray of breastmilk!
On a griping about airports note: why do they have a special line that strollers can use but other parents can't? Yes, babywearing is more efficient, but parents can still use the extra help and speed.