Now who is the winner and who the loser?
Depends on who's awarding the points.
Could be either one of them. Could be all of them. It's not like they were competing, or even playing the same game.
When your body isn't good for anything anymore and you can't even enjoy spending money, being happy about the people you created is more or less the only thing left - and you can really be happy about it. But that's only if you have a good sense of empathy for the happiness of people you care about.
Honestly it's a tiny assumption, nobody's perfect but it takes being terrible for your kids to avoid saying goodbye on your deathbed.
Winning is a category error at this point.
Not really. I think it's an interesting mental exercise and can see the pros and cons to all paths.
I think the optimal path is a mixture of all three. Work hard enough to afford the life you want to live (ideally at a job that is itself gratifying and meaningful) and then fill the rest of the time with experiences shared with friends and family.
Hiring and compensation is also quite ageist (this time not in the normal bad way!) where being thirty generally entitles you to a higher salary expectation than someone in their twenties.
However, I think there are just as valid arguments to be made for each of the people noted - some people would view the person with kids as having a burden to deal with through their thirties and other folks will consider the person who partied to have wasted their time possibly killing off brain cells and doing nothing "productive".
I think overall this is a really personal and opinionated question - I'd favor the career oriented individual as "failing" purely from a philosophy focused on enjoying and expanding the non-vocational portions of life, but we've all got different wants and needs - I hope the third paragraph helps explain the trade offs all three folks are making. The key thing is that nobody gets to live all lives - unless you're talking about The Egg[1].