It depends, some games that were designed within current limitations back in the day still feel good now. The trio from the golden age of mascot platformers (Sly, Ratchet, and Jak) are still a blast and I replay the Ratchet and Sly games every few years. They were designed within the limitations of what the early 2000's could do ans so they still look and feel good now. They're also single player, so it's easy to jump in and out.

But from a similar time of release I also loved Conflict: Desert Storm, which had 'realistic' settings and human characters that don't hold up well compared to the realism you can get in FPS games now, and the game was best played with a friend where each of you could control half your unit and plan flanks and rely on your friend to save yoy from danger and you them. That's not something I'd be able to recreate now, I wouldn't be able to play through a slightly clunky 15hr game with a friend and love it in the same way