If the question is when is the best time for a gambler to draw a line or stop I think it's clear that in a win or lose situation is a situation that is indeed highly recommended to stop, such as when you have managed to achieve a number of wins where stopping at that time can save you from the possibility of losing all the money that has been won which indirectly also saves you from regret.

And in a losing situation it is almost the same, everyone will never like losing money but in any case losing is a natural part of the game, meaning losing is natural but when the number of your losses is in a row then it is a problem, and that is why stopping when you experience the first loss is always recommended where the benefit is that you will avoid a much larger amount of loss at that time. This means that in two win or lose situations stopping is a wise idea to do, after all there is still plenty of time for you to gamble.