Exactly. I mean, you're going for the nostalgic element, so I'd fully lean into that. Bring back old windows media player, and winamp (maybe it increases productivity while listening to music) and old school applications so people can say "oh! remember when we used that one??". You can ask chatGPT which ones were the most popular applications on Win95.
Solitaire maybe? as a side quest? And you know what would be REALLY SICK? That the player can execute Doom (maybe just as a video or GIF of a gameplay, not the game itself) or another game, and every time the gameplay finishes you add a bonus to something, productivity or enjoyment. Sort of the same you're doing with the Copy-file Window, just play a gif.
Maybe enjoyment as a mechanic, it will decrease over time and you have to play doom or play a video on Windows Media Player to increase it back to green levels, otherwise you'd be penalized with slow productivity.
I know, I'm just brainstorming here, but you can do so much with the base you have that I'm excited to see what you finally come up with.
Anyways, good luck with your project!