I'm IC
SO i have no choice i wearing a diaper through an airport, and its not any big deal, not illegal and even if you get checked, ask for a private room if your worried about other.
Beyond that, yes you can check a medical bag with diapers, you shoud be IC to use this benifit but that is not easily or even able to be verified by anyone as you dont have to have it on your medical record per se. not to mention the airline doesnt legally have access to that anyhow HIPPA after all...
But, ethics aside, a checked bag with diapers is the best option if your flying with them.
I prefer to have ALL my stuff shipped to the destination prior to even leaving for the airport and verifying it arrived before i leave....
Used to contract mostly overseas and 99% of the time when flying commercial i'd have all my gear and personal stuff including diapers as i've been a bedwetter for life (one reason i was not able to be in the military) so need that to be there. Now flying private i'd load the cases on the transport of course and fly with it.
But myself i'd take a small caryon and nothing more on the airlines....just my preferance to not look for luggage...and working i'd ship 3-6 pallets of gear to the destination so a few bags of my personal stuff is not a big deal at all. 3 large flight cases for tools, 2 flight cases for for my personal stuff and then whatever supplies for the job made up the rest.
As for the fear of getting checked for drugs, dont worry about it unless your carying drugs, not a big deal.