I’ve lost data not realizing I was backing up placeholder files (iCloud).
Hiding the network always ends in pain. But never goes out of style.
My own approach to simplicity generally means "hide complexity behind a simple interface" rather than pushing for simple implementations because I feel that too much emphasis on simplicity of implementations often means sacrificing correctness.
This particular example is a useful one for me to think about, because it's a version of hiding complexity in order to present a simple interface that I actually hate. (WYSIWYG editors is another one, for similar reasons: it always ends up being buggy and unpredictable.)
Same. I lost a lot of photos this way. I've recently moved over to Immich + Borg backup with a 3-2-1 backup between a local synology NAS and BorgBase. Painful lesson, but at least now I feel much more confident. I've even built some end-to-end monitoring with Grafana.