I guess im sorta a resident expert on going through TSA (former flight attendant, now pilot) so heres my tips.
I usually put my wallet, keys, and any other pocket items in a coat/jacket pocket or in my roll-a-board (22inch tall carry-on bag..the one that all the crews have, black, perfect overhead size). All I have in my hands as im walking to the first agent (TSA or contractor) is my boarding pass and ID in one hand, my roll-a-board dragged by my other. Once you get in line at the actual x-ray, I put my Drivers License/ID and pass back into my pocket, take shoes off, everything on the counter and put em in the xray. As a habit I always pat my pockets before going through the metal detector. That being said, dont wear any metallic jewelry to the airport (a wedding ring wont set off the detector normally).
No liquids (except medications, sunscreen etc. under 3 oz a piece, and put it in a ziploc). If you have some liquids (medication, sunscreen, contact solution etc.) make sure its in small quantities (under 3oz) and put em in a small ziploc bag and have them ready to take out of your bag because they need to be out of the bag when going through the x-ray.
Shoes go IN a bin, just dont cover em with stuff.
Regarding packing...if it doesnt fit in my 22inch roll-a-board, it doesnt go. We had an issue with this the last time on the cruise so we had to check a bag...*GASP*....(I was a ramp agent, aka bag smasher, in college so I have nightmares about checking a bag). I usually have one roll-a-board and one "personal item" (aka Purse, Laptop Bag, small backpack...anything that can fit UNDER the seat in front you basically). This usually lasts me no problem (...I am a guy...) for a 5-7 day trip to WDW. You can weigh your bag on a bathroom scale to get a general idea of what it is, always remember that you always bring home more than you take!!! Leave a little space!
Hope you have a great trip, dont worry bout the TSA, not all of them are jerks
DH has similar issues..not afraid of flying...doesn't like Checkpoint Charlie and starts fretting about his expensive camera equipment 2 weeks out....don't get me started on the saga of the dueling CPAPs we use. So he takes Ativan. He is a big guy and the other problem he has is just the general confinement of the aircraft. So now we drive 2 hours west to New Olreans to fly 1:45 minutes east to Orlando--the only direct flight I have been able to find from Pensacola to New Orleans. The goal is to get him to our destination as fast as possible. I empathize with you on security, thank the Lord for Ativan.
