If you’ve ever had a cat sit in front of a toilet paper roll and spin it, you will appreciate having the open end toward the wall so it doesn't fully unravel
I’ve done something like this converting html to obsidian md. I interrogated gpt 3.5 with specifically what I needed to accomplish and went from there. If you can’t accomplish a formatting quirk in the same conversion process you might run iterative processes to accomplish them after conversion. I’ve done similar with BBEdit and vs code basically to find and replace across a lot of documents.