Sharky99 is on pace to conquer the Challenge with a record of 3-2-1.
At this rate, he would finish 15-10-5 with the pushes neither helping nor hurting his cause.
3-2-1
6-4-2
9-6-3
12-9-4
15-10-5
Extrapolating 4 more pushes is the exceptionally rare case, but it shows the 5th push helps.
To illustrate the much more probable case, if say you are at 3-2, your next pick will be W, P, or L so you will either be 4-2, 3-2-1, or 3-3.
Thus if there are no more pushes, you will need to go at least 14-10, 15-9 or 15-9 to be >=60%. So clearly that first push hurts as much as a loss.
Now let's say you are 3-2-1, and you need 15-9 if no more pushes. Your next pick (W, P, L) will get you to 4-2-1, 3-2-2, or 3-3-1, which means at least 14-9, 14-9, or 15-8 to hit >=60%. Thus the second push results in the same W/L target as the win, so it helps.