I would feel shit about losing their money just because I wanted to gamble so I don't do it.
You would feel like shit if you lost somebody a dollar? How about one cent? Even if there was a 1/1000 chance? Even if they stood to win life changing money on the other 999/1000? Do you think they would be upset?
Is no amount of loss worth any amount of win? If that’s your position, then how do you even get up in the morning? Why is this situation so different at the bar? Likelihood of things going badly in a bar are far far higher in my estimation.
you’re describing gambling
I’m describing basically every choice you ever have to make in terms of gambling, yes.