Here's what we do in the two Chicago area 14.1 leagues that I do the bookkeeping for (Red Shoes and Illinois Billiard Club).
Every player has a handicap equal to the points he must score to win. If a 100 player is playing a 70 player, he will win if he gets to 100 before his opponent gets to 70. Another way of saying it is that the 70 player gets a 30 point spot going to 100.
We play two games per night. If a player wins both his handicap advances by 5 points. If he loses both it goes down by 5 points. A split means no change for either player.
The system has worked well in that we seldom see a player get prize money twice in a row. If he wins money in one session, his handicap has automatically risen a fair amount in the course of doing so and that makes it harder for him to win in the next session - unless he's rapidly improving, which is a rare occurrence.
We can play shorter games than our handicaps. The two players can agree to play to a percentage of their handicaps. 80% is a common percentage but it can be anything they agree upon. We also have a special rule available to those who are physically handicapped in some way and are unable to play two long games.
Feel free to message me if you are in the Chicago area and are interested in playing in our leagues, or if you wish to discuss how we do things in more detail.
Rich Klein