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It is nicely established in the earlier seasons that Pacey and Joey are the ones without much access to money while Dawson and Jen and Andie have it easier that way. Remember Pacey doing the pageant just to get out of his house? (season 1 is really kind of super dark about Pacey's homelife - his father in particular.)
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And Joey's comment about entering to win so she can go to College because that would be the only way she could get out of Capeside.