Very often what holds you back is not a huge and complex thing like an AAA game, but something far less demanding and obscure. Something like an app to design knitting patterns, elaborate, purpose-built, and without a huge team behind it. Not open-source though. In this case, seamless compatibility is great.
(For games, there is Proton.)
For me (Well, my grandmother) it was Family Tree Maker.
To cut a very long story short - after Windows 10 restarted on her, and changed default browser and application settings too many times she was going to completely give up using the computer.
I built a new machine (a Dell AIO workstation) for her with Ubuntu, FTM and a few other things.
Worked brilliantly.