Not everyone is altruistic. Some people are just selfish. I'm not saying that it makes complete sense for a Corsair to tax someone going to Tripoli or for an Outcast to tax someone going to Valletta, but sometimes people just want money and they forget about their vices and virtues. It might be good character development, honestly.
On a side note, there is a Corsair Court about Corsair Laws, and if you were bringing supplies in, you can have him tried for treasonous acts.
[8:32:45 PM] Dusty Lens: Oh no, let me get that. Hello? Oh it's my grandma. She says to be roleplay.
[12:49:19 AM] Elgatodiablo: You know its nice that you have all that proof and all, Bacon... but I just don't believe you.