I travel fairly frequently for work and play. My thoughts:
1) Going through TSA security at the airport. First time I did it i was MORTIFIED. Like seriously mortified, to the point I thought I might be selected for, how shall we say it, extreme vetting. Took a moment to calm down, told myself it's like any other trip through security. Walked up, put carry-on into x-ray, got scanned, walked right through. Grabbed my bag and that was it. The whole experience was like getting a shot at the doctor. Once you get past the mental road block it's not a big deal. I've never had the ordeal of going to the "room", although those that have been through it mentioned the agents know lack of professionalism will cost an agent his or her job
2) Flying - Sometimes I fly padded, sometimes not. Usually if flight is over 3+ hours I consider going padded. If I need to go I try not to use my diapers in respect to my seatmates, if we're close to landing I just use my diapers. Never had an accident while flying, but I have had close calls. I'm sure others will agree it's basically impossible to change in most planes, only the larger wide body planes have enough room to change in. I always keep that in mind. I do know others that fly often sometimes try to break up long domestic (US) flights into 2-3 hour segments for that reason.
2b) Instead of flying - Anyone prefer Amtrak over flying? Living in the NE, I'll take Amtrak any day over flying. Not as fast but door to door is comparable, plus far more relaxed. For the padded among us, the accessible bathrooms are FAR superior to anything on a plane, and for me negate the need to even wear while traveling.
Anyone else had good/bad experience traveling Amtrak while diapered? Curious
3) Hotels - Been to tons. Diaper or double diaper up while there, wrap in it a grocery bag, put it in the trash. Like others have said, they'd much rather empty the trash of a diaper than deal with wet sheets and a mattress. Trust me, know from experience. I'm good friends with a hotel manager (large, convention hotel). He told me some crazy stories about what they had to clean up. Needless to say a diaper in a trash can doesn't even make the list.
4) Cars - If I'm driving I don't need to be diapered, sometimes (rarely) I do if I'm a passenger, as I rarely sleep in the car. On a side note - my old pickup truck was good for doing diaper changes at my farm. My Suburban was even better
5) I've never had to pre-ship diapers to a location, but I suppose it wouldn't be a big issue. I used to get stuff sent to hotels all the time.
TL;DR - Go explore. Diapers IMHO make it easier if you're IC.
~PPB