> Half the time I think a person wanting to rip off Windows (I know, I know) would be better off writing a Windows 95/98 looking X11 window manager and hacking it to only use Wine. Seemingly for free you would get tonnes of hardware support and the obvious benefits of Wine. You could even emulate the "upgrade whilst shutting down" behaviour to update Linux underneath. I think you could quickly end up with something that would pass at first glance.
This was attempted once with "Lindows" (later renamed to "Linspire" after the inevitable Microsoft lawsuit). Wikipedia informs me that they're actually still around in one form or another and owned by Xandros these days.
Apparently [1] Lindows -> Linspire -> Freespire [2]. There's also Xandros Desktop OS but that's apparently discontinued anyway [3].
I never personally used Lindows (or any variation of it), but I'm pretty sure you could create an experience that users would find pretty difficult to distinguish between Windows and Linux for the most part.
The key would be making sure everything is redirected through Wine and for the most part the OS does all the maintenance itself. Then it's just a case of wrapping some common utilities with a Windows like layout and it should be good to go.
Lindows was interesting. Windows was much more relevant then, not as much web stuff going on, no mobile apps. Unfortunately, Wine was not very feature complete, so it fell on its face quickly.
Lindows launched in 2001 IIRC. At the time, Wine didn't have regression testing, so someone hacked up a simple test-runner in C, called it "winetest.exe", ran the tests on Windows 95, 98, NT 4 and XP, and submitted it the Wine project.
The idea was to capture how actual Windows works, so Wine could implement how Windows actually works, not how you'd think it works just from looking at API docs.
This was attempted once with "Lindows" (later renamed to "Linspire" after the inevitable Microsoft lawsuit). Wikipedia informs me that they're actually still around in one form or another and owned by Xandros these days.