> Could the be a good "mom and pop" OS

Hate to be that guy, but if that's your problem just hand them an iPad or a Chromebook. Unsatisfying, I know, but it's not like my mom is Mrs. Roberts.

A WSL-like for Win9x is mostly just for the lulz.

No.

No one should be running Win9x for anything connected to the internet. Ever, full stop.

The only reason to touch it is for a dedicated retro gaming setup or (completely airgapped) for some industrial tool with drivers/software provided by a company that has been defunct for 25+ years.