The point at which there is a swing is when you start in the middle of the pack.
For instance, when you sit 24th, to leap over 23 teams you have a reduced capacity in how far you can move - obviously this is dependent on the pts the teams about you start with, but match to match, you can only outperform so many, and as you move through the matches towards the end of the season statistically those at the top are more likely to perform better.
From 24th, assuming results go in your favour, after game 1, your best placeing is 10th, because you can only outperform 66% of teams, after game 3 its 4th, game 3 its 2nd and game 4, 1st.
From 15th, game 1 is 5th, game 2 is 2nd, game 3 is 1st.
These are extreme examples that dont follow probability and causality but does highlight how a lesser number of teams but greater pts, still means easier progression up the table.