On windows there is a lot of (mostly old) software that don't work for random drivers/incompatibility. Proton/Wine is something that often you don't even have to touch in order to use as its integrated into steam, so I don't see why it should be a downside. Rather, I almost prefer wine prefixes over classic windows as I can decide a program which software should use without fearing weird versions mismatches or other errors steaming from global non-managed installations
I think it's refering to the fact that the reboot SimCity was a single player game (you could never play with someone else) but that was always online anyway
It should work, but I use tailscale so I can't personally vouch for it. I don't think it differs that much from plex tho, so if you are fine with it and you have already the pass, you aren't losing out anything major
Imgur should be awful for nsfw content too as they started deleting/already deleted all of it. I know of imgchest other than Imgur, but don't have too much experience with it
Italian here too. It's sad how the EU has to make us do the smart things as we are incapable of them