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You can't have to characters on the same account logged in at the same time. My son and I have two accounts, and whenever we accidently log in on the other one the person playing gets kicked off.
Incidently, one nice thing, if you have two accounts you can "seemlessly" switch between them on the main screen that shows your characters. In Toontown, you had to fully logoff and log back in. PotC is a little quicker to switch over.
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