Lots of cool stuff in here. I’m going to have a long look at Restic and Syncthing.

I’d like to know why Skim instead of FZF. They are pretty similar but I’ve been using the latter for years and would like to know of any possible advantages to it.

There's a lot of these pickers and they are indeed similar. I've been using https://github.com/jhawthorn/fzy since it's not fullscreen and has a really good matching algorithm.