

I also love the “files over app” approach, I am doing it more and more for simple stuff like (habit-) tracking. With the tempo that applications become outdated or even obsolete, I think this is something very powerful.
I think your radicale/caldav approach is interesting. Would you then also run radicale on your phone? Or simply not have the calendar on your phone? Would syncthing only sync in your home network too?
Thanks a lot for bringing yunohost up, this looks very very interesting. I will bring it up there.
When it comes to docker, I think at least Mac would be close to Linux (at least from my experience in my previous job – there are some integration issues, but managable I think). Windows I have no idea to be honest, could be a nightmare. For me the benefits of docker seem to be: isolation from the rest of the machine, and that pretty much every selfhostable app has a docker compose file.