Let's say when gambling, you follow a specific pattern. Let us use lottery for example. You bet on the same specific set of numbers. What would be more regrettable? Betting on the same set of numbers for the rest of your life and not winning or... changing up the set you bet on only for your old set to win?
Basically, would you rather bet on the same thing again and again then regret not exploring more or explore different kinds of bets then miss out on a win?
From this perspective I think the person should continue his trend on betting the same numbers over and over again and never regret doing it no matter the final outcome that can be several years of losing and never win it. If you change and then your numbers win this is a regret that will only go away when the soul of the person will go away meaning when the person dies. It is a feeling most persons will have for life that is why I never suggest to change what you have been doing for years. In the end in gambling everything is regrettable when it comes to losing money, that is an universal feeling that no human being likes to experience.