Anthony,
I just barely have you beat - we leave on Saturday! :)
Pin Trading Nights are lots of fun! You can meet collectors and amateurs alike, see rare and unique pins, and expand your own collection. The Disney info can be found here:
Pin Trading Nights.
You are never obligated to trade! Very important to know. A trade should be something that is fun and valuable to both parties, so if you are not comfortable with a swap then don't do it. In my experience you will find a mix of serious and casual collectors, and a few 'pin sharks'. Trust your gut if you feel that someone is being pushy.
I don't want to alarm you! Most pin traders are in it for the fun, and will enjoy talking with and educating you just for the love of the game - no trade necessary. but there are those who take it very seriously, so proceed with caution.
There will be lots of cast members around, and they are actually my preference for my daughters to trade with. It's a safe, un-intimidating way to get started.
One tip - look for cast members with pins turned backward. They won't be able to show you what it is so it's a blind trade, but trust me - it's turned backward for a reason. My 5 year old loves the thrill of the hunt looking for a backward pin! (And if you see three little girls all dressed alike, go easy on them with the trades ok? ha, ha!)
Have a great time!