You
Long branch or a flag behind main?
ChatGPT
Flags for anything longer than a few days. A branch that lives two weeks becomes a merge event; a flag makes the same work a series of small changes. The cost is discipline about removing flags, which is the part every team underestimates.
You
Is there a simpler version that gets most of the benefit?
ChatGPT
Yes: do the first step, skip the automation, and revisit in a month. Most of the value is in the first step, and most of the cost is in making it repeatable before you know it is right.