Based on this post I’m gonna say take it slow with a dual boot or live installation, if at all. You mention a lot of IMO fairly minor and subjective look and feel type criteria that indicate that you’ll be quite bothered by minor changes. Using Linux is going to involve major changes. If you’re not willing to leave your comfort zone and relearn a few things, might as well stay on Windows.
I think this is very deliberate. Having played at least a chunk of all 50 games, there are only two or three that I think would have benefitted greatly from more instructions or tutorialization. Figuring out how each game works and being surprised when you find a new way to use the very simple controls is part of the experience.