Show & tell: workflow tweaks — am I overthinking this? [v5]

There is a lot of conflicting advice online and most of it is from 2019. The trade-offs here are not obvious to me and I keep flip-flopping.

The trade-offs here are not obvious to me and I keep flip-flopping.

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.