I think smaller commits and fewer long lived branches are good. Feature flags are good. Breaking stuff down logically is good. But this example seems inefficie

I think smaller commits and fewer long lived branches are good. Feature flags are good. Breaking stuff down logically is good. But this example seems inefficient. Keep that original failing branch in a seperate clone to refer back to. You can even pull down the fix commits back to it to observe the test count improve gradually! And with dependencies certainly in .NET and Node and probably Ruby too there are dragons in the details. Let the compiler and/or tests do that heavy lifting rather than a tree if postit notes. For example you assume you know upgrading gem A will need changes XYZ but I bet ya there are gotchas related to when you upgrade B and C along with A. Picking the granularity level takes a nose for it but I wouldn’t waste time planning just start chipping away at the problem to help get a lay of the land. It feels like this method is like planning your walk to the shops and creating a survey of dogshit on your path. Just get walking and look where you walk!