Looking for unpopular opinions — what would you do? [v1]

The trade-offs here are not obvious to me and I keep flip-flopping. Not sure if this is the right place to ask, mods please remove if it is not.

I tried three different approaches and none of them felt quite right. Not sure if this is the right place to ask, mods please remove if it is not. Mostly thinking out loud — feel free to push back hard.