I really want to switch to Linux full-time, but gaming keeps me here on Windows (I guess there have been LEAPS and BOUNDS of progress since I first attempted to switch over in 2014, buuuuut)
I'm still relatively inexperienced with Linux myself, I just finally switched to Ubuntu 18.10 a month or so ago, but I did want to mention that there's a Linux steam client without the use of Wine. Although still limitations on which games will run. But I have, indeed, heard a few people use the setup you mentioned to work with a Windows-functional version of Steam.
Unfortunately, no. Some digging suggests it highly depends on the game, but I ran into some comments that mentioned the steam workshop works fine in Wine and the Nexus Mod Manager works fine in a virtual machine. Also you can pass the Wine drive to a virtual machine and operate it like Windows, too.
Not that I love referring people to reddit but /r/linux_gaming might have a lot of answers for you before you put the work into setting it all up.
@vrysius awesome! Thanks for that, it sounds like the level of modding I’d be looking at is very doable. There seems to be a looooot more support for Linux gaming in general than the last time I tried.