Put the game on speed X20, that way you can beat it faster. Also, take short routes at the beginning of the game, and take longer ones when you're heavily armored. I beat the game. What I did is join the good guys to start the game, and then screw them and join the bad guys to make more money. You can only conquer cities as a bad guy.
It is, just takes about 5 times to get them there. Just take routes to the closest cities near the one you are at. Cause if you die, you can continue game and still have the same amount of money and other stuff. Also you start off at the city you were at before you died.