Sounds like your friend is absolutely not the target audience for a linux-based operating system. If he wants to play Windows games and use software designed for Windows, then he should be using a Windows OS. Anything else would be providing a suboptimal experience for him.
Personally, I’ve been using various Linux-based systems since 2004, as a software developer I use a lot of command-line utilities, and many tools and applications designed for Linux. If I were using predominantly tools and applications designed for Windows, then I would be using Windows. No need to make life more difficult for yourself and others.