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My advice is what others have touched on, eBay is a awesome spot to find old pins and score good deals on pin lots that can be used to trade with. Just be wary of fakes! ALWAYS buy only from someone with a 100% or 99% feedback that has several transactions. It is a plus to buy from someone who also specilizes in pins, as this increases the chances of getting real Trading Pins and good ones at that.
I usually buy 50 to 80 pins off eBay in various lots pre-visit to specifically use for trading with CMs. I would recommend buying a small lot on eBay, maybe 25 or 30 to start with. You will be amazed at the cool pins you will see being offered for trade by CMs and other Guests! I have better luck trading with CMs as a lot of Guests are either serious collectors and trade only for similar collector material, or just not interested in 'generic' simpler pins i usually have from the lots. Do not get discouraged if Guests are not up for trading. All CMs will always say yes to a trade...and they usually have exclusive pins. The interaction you will have with them is always enjoyable as well!
Trading with other Guests and even Locals can be fun too. A GREAT spot to meet up with enthusiastic Pin Traders is Downtown Disney on Thursday nights at the main Pin Shop. Locals arrive with huge binders PACKED with pins and are usually very open to trading even the most simplest pins. It can give newbies to Pin Trading a real sense of the incredible assortment of Pins that are actually 'out there' and the amazing diversity. It is great to just look through their stuff. Same goes for EPCOT's Pin Central near the Fountain of Nations on weekends. Many locals show up with binders and welcome people to view them even if you are not going to make a trade.
A note of caution though if visiting these two places however - BEWARE of anyone wanting you to buy pins from the shop or stand to trade for a pin of theirs ! Chances are what they want you to buy is Limited Editions in trade for common CM Lanyard pins that can be found elsewhere for a few dollars on eBay, or for free on a CM lanyard. I fell into this trap some time ago. I spotted some Cast Lanyard pins i wanted in someones' binder but they were not interested in the pins i had for trading. They suggested i buy certain pins they wanted from the shop ( all Limited Editions, the more expensive pins of course) to use to trade with them instead. I did this for two pins ( sucker that i was...) but then realized what was happening. The last pin i was about to trade with them, they wanted TWO pins for their one..which immediately threw up a red flag. It is a general rule in Pin Trading that you trade only ONE pin per pin, no matter how fancy or rare it is. So i declined and realized i was getting duped. So just a heads up - their are people out there who prey upon newbies. Be careful!
Always try to be aware of the pins you have so you will not be taken advantage of by 'Pin Sharks' . This was a problem some time back, perhaps still so, thus why the Pin Trading Nights at the various Resorts stopped. Be cool and have fun...just be aware.
Pin Trading is a lot of fun and makes the visits to WDW or DisneyLand all the more enjoyable. The 'thrill of the hunt' and the delight of finding a favourite character pin makes for a nice additonal vacation memory.