Update: I tried pass for 48 hours. GPG key migration was fine, git setup was fine. Then I realized I need to rotate a database password across 17 boxes and I'm back to wanting a web UI. Pass is great until it isn't.
Currently testing: sops + age with a git repo. @annexbi you got me curious. One encrypted YAML per server, decrypt on deploy, zero persistent secrets on target. Still figuring out the key distribution part.
Also @liam_funky your HostHatch+SSHFS thing is growing on me as a fallback. $3 is hard to argue with.
I accept this diagnosis. But I also accept that I have 52 passwords.