I meant to reply earlier, but the afternoon got away from me and I just sat down again. I checked the list you sent, and the second option still feels like the easiest path because it keeps everything simple and does not require extra back and forth later.
I also think doing it in small steps will make the weekend smoother. I usually start with the part that feels more annoying, then everything after that seems easier. If you want, I can help sort through the notes tomorrow and give a quick opinion on what looks unnecessary.
I am around in the late morning, then free again after dinner. If your schedule shifts, just send me a short note and I will adjust. No rush on my side. I mainly wanted to say that your idea makes sense, and I do not think you are overcomplicating it as much as you think.