I think it makes the most sense to do it by region. For example, figure out everyone in NY/NJ/PA/CT/MA who wants in. Pick someone trustworthy to handle the cash money. Someone like Ehrik comes to mind. And then just divide up the total cost and use Paypal to give him the money.
Nice thing about doing it by region would be that you could have an event after it ships and everyone can just pick one up rather than going through the trouble of reshipping it.
But I guess it really depends on how much the shipping actually is though. It may not be worth the hassle.
It may make more sense to do smaller groups... like me, Pincher, Chibi, and Zaelar for example. (Bergen County Represent!
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