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I don't know why, but I couldn't even win a round at that ranch. I ended up just doing it at Saint Denis as it is so much easier. The AI there doesn't cheat as often.
As for when you should quit, usually if my opponent reached 60 points or higher I quit. Also, if my opponent managed to score like 40+ points in the first round, I quit.
While I'm still working on win 3 rounds without drawing (F'in guy has won like 5 rounds vs me yesterday when I was about to win the round...did 3 in one game even ...) I find playing in St. Denis easier. I really like the 5's version, easier to do the math lol.