http://www.simplicitycomputers.co.uk/ was started in late2008 (I think) and made "elder" type OS solutions the key part of the project. This is built on top of MintLinux but it could have been built (with more work, and a valid Microsoft Product Key) on top of XP/2k or perhaps even Vista/w7/w8. Most of the guys I know who did overlay utilitys have moved from windows to avoid some of the harsh restrictions.
I think there is a place for Microsoft to keep making OS's, Personally I see no glaring problems with the things they make. A lot of the problems people are complaining about are UI or Non-Working hardware.
Non-Working hardware tends to just be down to lax driver support, and in recent years it has gotten a LOT better. I am sure a top of the line BD burner or the newest 11ac network cards migh thave issues, but they will have those issues in Windows too! Once every MFGR starts releasing drivers for their hardware to fit multiple platforms then that will not be a problem. In fact, I have seen some AppleOnly hardware work in Linux based PC's because that community can sometimes get drivers working.
The UI problems are simply down to the fact that users are so stuck on using one configuration that they really struggle when they move to something else. You can take someone from a car they have driven for 10 years and put them in a different MFGR's car and have the same sorts of complaints. A lot of people want it to look and feel just like Windows. Look at the move from windows7 to windows8 Touch Mode, people are up in arms about it. With the dominance MS gets out there this wll be pushed to millions of users who think they have no other choice (GNU, Linux, OpenSource, whatever) and they will adapt. Those users will then look at Windows7 and laugh at how crapy it is, they will also look at the GNU offerings and say how crappy those are.
Ubuntu has recently came under fire from Stallman for some of the same reasons that W8 is currently under fire. Keep in mind that there are times when Apple and Microsoft have not been on the bad end of the stick from the GNU crowd.
Locking down hardware and software is just the way it is, If you can force your userbase to rotate every 4 years then that's a lot of income. 7 billion people who buy a new os every 4 years, a lot of potential there.
I am not pro or anti MS, the are just another global corp who will do what it takes to win, even if that is not legal or ethical. The GNU crowd wants a "free" society where users are not put under huge restrictions and requirements, It is a nobel goal.
It is not just software that has the ills that GNU / MS / APPLE fight about.
I have a set top box more powerful than any roku box. It is hardware-locked by the vendor so I cant update it to support things like Netflix, games, or proper network streaming. It is Abandoned by the MFGR (Pace) and they released newer (low spec) hardware that has more bells and whistles. In the world of FSF/GNU My hardware would be good for another 10 years.
Try putting windows7 on a 486 JUST so you can have the latest microsoft browser JUST so you can view web pages. Try ripping your whole CD collection using Windows Media Player with the DRM option enabled and then buy a new PC ;P....
If you cant see the problems at that point then you truely have your eyes closed.