I think the Might and Magic series covers both ends of this.
On the holding up well side, the World of Xeen games (4+5) have a really vibrant, distinctive art style that still looks great today, paired with gameplay that I think nicely straddles the line between more unforgiving CRPGs and accessibility. It's really one of the best RPGs ever made.
On the other hand, the next few games with their transition to 3d had some issues. MM6, 7 and 8 are not pretty games. MM6 was the worst by a longshot, and while MM7 did improve a fair bit, it still wasn't much of a looker. MM6 Also suffered from being the first game to radically redesign the core gameplay mechanics that had remained more or less constant from 1-5. Again, MM7 refined these quite a bit, and in that regard it actually has aged really well, it's one of, if not my all time favorite game (But DAMN is it ugly!). MM8 on the other hand, didn't really improve on 7 at all, and coupled with some really questionable design choices, probably took a few steps back as well.
We don't talk about Might and Magic 9...
Overall, it just feels like New World Computing never found their feet after MM6.
This post could have been written by me. Probably. Really, I don't think Might and Magic VIII holds up all that well simply because it's kind of a mediocre game all around, whereas I think anyone willing to look past the graphics could find VI and especially VII fairly accessible as far as old CRPGs go. World of Xeen similarly, though I only beat half of it and cannot claim to have finished the darkside. It's a nice contrast from something like Wizardry 7, which while clearly a good game, wastes no time kicking the player in the balls with tough enemies.
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