If you're trying to get ancient software to work I think "user friendliness" is the least of your concerns. Especially compared to the alternative (Windows) where the answer is just, "No: That's not going to work no matter what you do."
Well given most diehard Linux fanboys despise any sort of containerized apps, aka AppImage, Flatpak or Snap (I personally only despise Snap), I'm going to say no.
Most people will need internet connection to Google specific commands to run or install the most trivial things, and it won't always work depending on what distro you're using. Oh you're using MX Linux? Goodluck downloading a Plex client installer and just clicking it to install. Maybe use Snap but then good luck creating a shortcut with just a right click.
Limux won't replace Windows anytime soon, not if even enthusiasts need to Google almost everything.