I've been maintaining an emulated Pentium Pro 200 MHz Windows 95 machine on 86Box for some time with all my favorite old software from childhood. It's great for nostalgia, and if friends come over they have fun showing their kids things like SkiFree, Jezzball, and Encarta 96. Still holds up great for kids.
Yep, I showed my little ones Odell Down Under in the browser at one point, they loved it. A certain amount of that old software I copied to .iso from my physical CD's, but not sure where I could grab something like Encarta 96. Legally.
Had also been thinking about asking Codex to boil the oceans in an attempt to fully decompile or reverse engineer that OG of 1990s 4X games, 'Stars!'*, which I have a copy of, so I could have something modern and native for MacOS that kept all the mechanics. Maybe I should just do this instead, will have to investigate.
I think part of the reason it holds up still is things had to be designed for newcomers at the time, since people largely were.
Cinemania 97 was a big part of this era for me too, though it was far less widespread than Encarta. Fantastic resource for classic film, and into the 80s and 90s, though it was bit quirky watching it get further and further out of date, like the big 1999 films that defined my youth (The Matrix, American Beauty, Fight Club, etc) all completely unknown to it of course.