Not sure what OP is using for their photos, but Google Photos handles all of those mentioned features automatically for me. I’m sure there are other similar apps that do the same.
I wonder if Face ID is still able to partially detect a masked user's face, just with a much lower confidence interval. Maybe the presence of the watch allows Face ID to lower the confidence threshold when it detects a mask blocking half of the face. This is just a guess, I have no idea how Face ID works.
If Face ID can't detect anything when a user wears a mask then I completely agree with you. It seems really silly to require the mask in order for the watch unlock to work. I don't understand the security model there.
Would be interesting if you could treat each service (Youtube, Docs, Reddit, Messenger, etc) as a “disk” and stripe your data across them.