You are better off staying in jail when all the properties have been bought up on the game board. Doing this is less risky than landing on someone's property and you still have the option to trade and mortgage.
Piece selection matters
Picking the race car, out of 50 games using the racecar myself, letting someone else be it or against the AI, race car 75% of the time is the winner. Just a tidbit of tips for you there.
