I think I have a fairly good idea of where I’m going. I’ve been using my old gaming rig as a Linux self hosting server for a few months now, I’m confortable with the Terminal and SSH. Kind of understand the file structure, but not as instinctively as Windows for sure.
I’m more worried about the friction of not having every software I wish for instantly available.
For instance, I use MusicBee to listen to my music library. It’s been the case for over a decade, so I’m not sure where I’ll go.