If you are the better player and want to get all the cash the quickest way is to play 2 out of 3 for xx dollars. The weaker player will rarely ever win 2 in a row so the money will constantly filter to the better player. When I was on the road with a couple of great players the young one would always try to go in by themselves and play 2 out 3 league rules 8 ball. He would almost always get in action with this and it was the quickest way to make the daily nut.
When I was playing a lot of pool in the 60's and 70's, many games were played Five Ahead. I played tons of "five ahead" matches, typically five ahead for $50, which was good money back then. It's not so long and it's not so short that a weaker player might win. It was the perfect length match for a better player to win the money and not get lucked out on. We also often played Races to Eleven, anything shorter was a fairly quick 9-Ball match.
I personally preferred the "ahead" matches, less chance of someone lucking out on you. You couldn't get beat 11-10 that way. The better player had more of an edge in this format. Often you were playing someone who was close to you in speed, there were so many pool shortstops around in those days. So if I'm going to play a guy that maybe I'm only the eight ball favorite over, I definitely wanted to play an ahead match. Yes I was a careful gambler back then, but it was my livelihood and I didn't like to book a losing day.