Maybe become rich from gambling will be their reason for still playing gambling. And they still enjoy the process even if that can give them more losses. They will not think about the money, but they care about the outcome.
Being very hones't I am not really sure what you are trying to say because your statements sounds contradictory to each other. Look everyone wants to win money and that's the basic aim when you gamble no matter if you are gambling first time or if you have made million bets, there is no fun in watching dice numbers rolling over your screen and I can't see how someone would have fun in the process.
If they cannot win, they will try over and over, and of course, they will use more money to try their luck. They hope that one day they can win the games so that they can give them the money, but if they can calculate the winning money versus the losing money, the lost money will be bigger than the winning money.
No one tries to win the game, people try to win bets they make at certain games. I agree on that last statement you made because no matter how much anyone brags about their gambling skills and maybe sports prediction accuracy but eventually they all are at lose in long term.
Overall I do believe, fun seeking gamblers are loving the process of gambling whereas profit-seeking gamblers are bothering about the outcome of gambling. If you love the process then you could enjoy your activities while you are gambling and this is how, I do believe we must gamble.