I'll add to the discussion as I have been travelling for work since about 5 months after 9/11 (good timing!).
Early TSA was a shitshow, no privacy, rooting through your suitcase in front of all and sundry. Things have improved over the years, at least their is little unpacking being done.
I had several notable instances where I had to go through security still diapered and had extra questions/screening. One early example, the TSA agent had to have me raise my arms so he could check my waistline. My diaper was sticking out above my pants a couple of inches; it took me by surpise. He immediately stepped in front of me to block line of sight to other travelers which was much appreciated and tells me it isn't the first time. Another time I was in a disposable with a heavy PUL velcro cover over it. The waistband apparently felt like a money belt to the TSA agent and I was taken to a private room to show them what it was. I was so flustered when they asked to see what I had on that I dropped my pants and had half of one velcro fastener undone while explaining "I have to wear these..." before they stopped me and told me I was good.
Other than that I made the mistake of bringing talc through and having it flagged. The young woman was blushing furiously as it was in the same compartment as my diapers. Never again!
