Mathematical chance vs real life

1/2 and 1/4 + 1/4 would be the same chance, as are 10 dice vs 10 rolls of 1 dice. But I am not here for math, it's about reality.
You know the guys in your simulation all had the same odds. I wanna improve the overall odds, a method where more people would win.

And if you consider real life end points;

• like if you play til you win. This could happen on roll 11 of the singular dice, but for the 10 rolls it must be the 20. So the payout is lowered by 9 bets.

If you already won 17k you may decide to keep on playing til you win or lose 2k.

Or you start with 7k, stop playing once you hit 2k.

These situations are real, you know the overall chance to win at 50 spins is the same but you won't play exactly 50 spins.

In the simulation/real life there must be some super lucky gamblers, those win more often by pure chance and that should happen slightly more often in a group of people playing only 1 number vs people playing 2/3/../17 numbers at once.

*and of course much more often in groups playing better odds than only numbers.

Yeah one is always an idiot when playing but losing 5 bucks on a roulette table is fun. 30-100 bucks is fair price for a fun evening. I just want the most bang for my bucks.