It depends on how often you come close to winning a bet or how many times you have won your bet. If you have always been losing, you would be tempted very much to cash out or if you have a pressing need for money. Anyway, we all deal with cash out differently. Some gamblers don't really like the cash out option, they feel it deprives them of the full potential winning when they cash out and it wins but what about when you don't cash out and it loses, those gamblers who support cash out have that as a reason that they use cash out. That's individual differences in gambling and the use of cash out.
Gamblers who often take the opportunity in every gambling they do will not make a victory of the responsibility and I am sure they will continue the remaining two matches. Of course anyone will be tempted by the previous victory, but when we put a small money continuing the match is the most likely choice. Back again as you say that it depends on how each individual responds to every possibility that will occur and can minimize the risk of defeat is also not wrong if you want to take cash from the previous victory.
Well that depends on if he is an active gambler that does a high staking but I doubt he is, the more reason he came to solicit for advise. If he is an active gambler, he must have been seeing such cases and would have by now decided on how to be handling cash out issues. There are different levels of cash out, small or big cash out depending on how much used in the staking and if the gambler won't have high blood pressure if he allows the cash out go and ended up not winning the game. I think he is not a big staker and that money would be very much needed to him.
If he is not an active gambler, maybe the opportunity to continue the remaining two matches is unlikely, but in accordance with the renewal he submitted has continued. I agree that active gamblers do not need to ask for advice to continue or withdraw cash because they know how to handle gambling. He also said that initially involved with small capital in gambling, only he was confused to continue or stop with a number of wins he had obtained. It was entirely the decision because we never knew how the real incident after he made a post and the picture taken.