We went through numerous years of that before Steam became a thing, almost a whole decade passed between the Internet getting popular and Steam really taking off. DRM filled DVDs and online installs with activation limits were the results.
> but let's not pretend that it was simply impossible to play Windows games before Gaben graced us with his attention.
Let's also not pretend that fiddling for hours with Wine configs is somehow similar to pressing "Play" and having stuff Just Work™. That extra level of polish that Valve provided is critical for making it actually useful for the masses.
> Do you have evidence that courts would see this differently with a digital download?
Can you show me a place were I can buy used digital games? Itch.io doesn't disallow reselling games as far as I can tell, but yet we don't have a used digital games market. Buying a random .zip file, with no proof of ownership, is just not something people are interesting in.