Persistence is something I care about, Tmux allow that between different sessions, local or otherwise, Windows Remote Desktop also makes it simple to continue work remotely. What bothers me is that the OS will eventually need to reboot, and the user is expected to reconfigure the sessions afterwards, at least partially.

I think a modern computer should be able to update its software, kernel included, in a way that the state of the userland could be kept, even with an actual reboot.

Check out tmux-continuum and tmux-resurrect plugins.