Yeah, modding you mostly have to do manually, but it's pretty easy. Most modern games that's just moving a bunch of folders into a folder the game has. Nexus is working on a Linux version though so hopefully that'll be ready soon, which should cover the majority of games.

As for running the games (not emulation, WINE stands for Wine Is Not an Emulator), you don't really have to do anything. They almost all just work. You just click play through Steam (or whatever you're using to play, Lutris is a good option outside of Steam) and they launch, just like in Windows. You can choose to tweak things, but there's no real need unless you want to do something weird.

It's more idiot friendly than you'd expect. You just have to enter it knowing it isn't Windows, so some thing will work differently than Windows. If you expect identical behavior to Windows then it can be annoying. You had to learn Windows at one point too, and you'll have to learn how your Linux environment behaves too.

I would recommend something with KDE (a desktop environment), because it's easy to use coming from a Windows user. Maybe Fedora. Just try it with a live USB and see how it feels. You don't even have to install it immediately.