This is explained in the story in Chapter 6. It's also a huge part of understanding Dutch.And as usual in Rockstar games there is a huge disconnect from story and the actual situation in the game. The main character and his friend keep complaining about money while you sit on 10k+.
And this is just rockstar inconsistency. Some missions are disappointingly railroaded, like the oil factory sneaking one, but others let you do different stuff, like the getting micah out of jail one.Main problem with the game was how rail-roaded the missions were.
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