Yeah, XP would definitely have more issues. 98SE probably would have the best all around compatibility. But there are some Win95 games that only run on Windows 95. The computer you’ve got is really nice for the 1994 - 2001 era, though. What you could do is get a pullout tray, and have different drives with different loads, and switch them out as needed. Ultimately, if the games you want to play work, that’s what matters.
The differences are a lot more than the current state of affairs. My great great grandparents were serfs, so I’ve heard quite a bit of stories about what it was like. As bad as stuff is right now, we are still worlds better off. Thanks to relatives that are still there today, I’ve been to where they lived during the serfdom, and saw the work they had to do. They slept on what looked like picnic table benches. Two people per bench face down with their arms and legs hanging over the sides. One tiny house, for a family with 7 children. They were constantly sick and weak from lack of food, despite growing it. Almost everything was taken from them from the insane taxes. Moving was not an option because they were bound to the land. Every day, they had to walk up and down a mountain to tend sheep. The one advantage over slavery is that they could only be bought and sold with the land they were bound to. So families couldn’t be split apart. It was also illegal for owners to murder their serfs. Slaves, on the other hand, would have been legally considered dead in the court of law.
That said, the oligarchs absolutely want to bring back both serfdom and slavery. Prison labor will be the means of slavery. Freedom cities will be the path to serfdom. The fact that there is a long way to fall to get to that point should absolutely terrify us because YES, it gets MUCH worse, and yes, we are taking an express train straight to that dystopian reality. There is no bottom for billionaires. There is no road too low. The most horrible things imaginable are part of their plan. The road doesn’t stop at late stage capitalism. Late stage capitalism leads to oligarchy, authoritarianism, and corporate feudalism. And the horrors of that we cannot yet comprehend.