I bought my first Mac in 1989. I bought my first non-Mac PC in 2015 and stopped using Mac altogether.
Basically at this point I'm recommending everyone to forget about iWorks apps (even though I brought a few people onto them earlier). I'm still holding on to Keynote even though the version compatibility issues are absolutely horrible, but it still produces the best presentations with the least effort, so I'm biting that bullet. To everyone else who's still using the old Keynote: Don't even think about trying out the redesigned one, nothing will be compatible anymore, just stick with it as long as you can!.
Meanwhile Google Docs impress me more and more.
Windows file sharing (at least with Windows 10 Pro) is pretty broken as well. Transferring multiple large files (especially 2 GB+) from OS X to a win10 file share seems to fail every time.
Not going to happen. Metal is the One True Way now.