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What I did is I would go to Tutnik's shop to sell things there for a while, until I get 2-4k. Then I'd go back into Enterpriston and spend all this money on loan and taxes. Then I'd go back to Tutnik and repeat.
The most important thing is : Your debt doesn't increase if don't meet a tax collector. Only your taxes are. So you can "stop the clock" so to speak.
Can't tell you which challenge though, had all four active.