As far as OS are concerned:
1/ Windows:
In my case windows 8.1 with classic shell work like a charm I don't know about 10 I don't usually install adwares on purpose on my computers
.
I think I tried 7 once but I dont remember running any utilities, with 8.1 I run war2, observer and insight all at once with a batch file and it works pretty good out of the box.
(I also tried pudbrowser and map editor for science and it also works fine)
2/ Linux:
I dont know how linux handles wine nowadays
I usually dont use linux for playing myself but it might be worth looking for that too.
I heard it is pretty stable one good thing about it is you get to try that for free and if it does not work well you haven't lost much.
As far as linux distros are concerned Id go for Mint or Manjaro if its a first time linux thing they are userfriendly and quite popular.
Also for graphic cards if you are going to run on linux you will want to get a Nvidia with the proprietary driver they are better supported.
Also I cant tell about the various utilities obviously if anyone runs linux they might have more insight than me no puns intended
3/ M.....Nope just kidding there is no 3 (: