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Well you need $10,000 for an AWESOME license and $20,000 for a CRAZY license.
It's not that difficult. Probably the best tip to get higher scores is try not to hit any other cars on your way to a destination. Every time your cab goes closely past another vehicle your customer gives you a tip, and the longer you go without hitting another car, the tips get bigger and bigger. With multiple customers, this just builds and builds into massive amounts of cash very quickly.
Another tip is at the start of a run just pick up red and orange customers. They don't want to go too far and they are usually pretty easy to get to their destinations with a "speedy".
Learn to drift the cab sideways into destinations by pressing X+B+Brake. Slide it in just to get a few extra tips.