Just curious what the oldest game is that you've played, and whether you enjoyed it or not. I'm less interested in the technical experience, so you can use the original release date, even if you played a more modern implementation.
For me, Fate/stay night just barely beats Clannad, by a few months. Both were released in 2004, and both show their age a little bit (Clannad in its convoluted branching, Fate in its resolution options), but are perfectly playable. But of course both are super popular classics, so I wonder if you all had similar experiences with more obscure or older titles.
Dividead from 1998. It was one of my first visual novels. I suppose it was alright. I enjoyed it at the time but didn’t have much to compare it with. It was a mystery vn with a map of a school where you picked where to go and most of the decisions were made this way.