I don't really know the current state of Ubuntu (the Linux distro I'll assume the laptop you would get has, considering its widespread popularity), but most big distros (I used to use Mint 17) try to be easy to use like Windows (some even mimic its GUI layout) nowadays. Of course, as soon as you are confronted with a very complicated problem, you may have to open a commandline-interface. There's also plenty of technical support forums for Linux, so if you're willing the learn along the way, it's not too bad, but yeah, gotta be patient when bad luck strikes.
Since the laptop comes with Linux, you probably won't have to worry too much about the driver maddness (Display working wonky, poor performance, not being sure what one to install, proprietary driver vs opensource driver...) that can ensue.
Wine support is also much much better in Linux than Mac OS, so I doubt you'll have many problems there. FeralHeart runs just fine for me in Wine. Infact, many Windows games run pretty good in Wine. If you got any other games in mind, I suggest you check out the Wine Application List before you make a choice, if any other games are a deal breaker for you. (
https://appdb.winehq.org/)
Another option down the road would be to dualboot the two operating systems, but get ready to install/configure some bootloaders! Or just use Windows. Up to you, but both seem pretty viable for FeralHearting.