We were originally planning to use FedEx Ground ship pins to our hotel. I went to FedEx on a Monday for a Thursday evening trip, and was told it would take three to five days (although the FedEx web site said three) and cost about $25 including insurance. This was not acceptable to us, so we decided to see about hand carrying.
We keep the trading pins in a Samsonite Hard-Side Rolling suitcase (about 20" x 13" x 8") which weighs about 35 pounds. I brought along a 1/4" bicycle cable and strong padlock, which could be wrapped around the suitcase in the event we had to check it.
When we went through security at Dulles Airport they stopped the conveyor and the operator had two people come over to look. We tried to nicely explain that these were collectible pins. Anyway they had us open the case, which we had expected. When they started to go through item by item, we asked them to take us out of public view, which they did by taking us to their nearby breakroom, which had tables. It took two people about 15 minutes to go though everything and for us to repack the bag. The only thing they would not allow us to keep with us was the cable and lock, which they felt could be used as a weapon. I had to take it outside Security, while Judy waited for me, and I went back to the airline counter where they put it in a box and put a luggage tag on it.
When we left Orlando again they stopped the conveyor and had someone look at it. Then they had one person go through the bag, but he just lifted the clear plastic bags and looked at them instead of going through everything. This person was much faster, but not as nice as the people at Dulles. He also had two armed National Guard troops backing him up in case we were to cause a problem.
One last item, the two Disney shops in the 60 to 99 area had many different pins for sale (inside the security area) including the special limited edition WDW/Orlando Airport special.
One side note. Going down (Oct 4) we ate at the TGIFriday's in the secured area at Dulles. They had no knives, even plastic ones. I asked the waiter how a person could eat one of their steaks, and he told us that steaks were off the menu. On the way back (Oct 8) we ait in the secure area at MCO and did get plastic knives with the meal.
In general, you should have no problem with pins. However, when they are going through your bags, stand back a bit (don't crowd them) but ask, if they are going to do a detailed search, that you be taken out of general public view. Also, once they have gone through your stuff, tell them you would like to repack your bag to protect from breakage.
