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I just use Lutris now and it all works, there's no more screwing around with Wine for me; if you had problems with Wine in the past, I suggest you try Lutris, you might find it is no longer a hassle.

If you use Steam, it's all automatic and transparent in the background, but I don't use Steam for everything.

how do you get those games onto the machine if it's offline these days? Unless you exclusively buy off GOG, and download the offline version...

You could look into LTSC, it's about as close to W7 as you can get in terms of user control (e.g. no forced updates) and still enjoy semi-recent Windows features like D3D12 ""Agile SDK"" (lol)

Are there games you want to play, that won't allow you to start the game if you don't have an active internet connection?

Don't know about him, but if a game requires an internet connection at any point, it's not a game I want to play.