The first prompt (with o1) will get you 60% there, but then you have a different workflow. The prompts can get to a local minimum, where claude/gpt4/etc.. just can't do any better. At which point you need to climb back out and try a different approach.
I recommend git branches to keep track of this. Keep a good working copy in main, and anytime you want to add a feature, make a branch. If you get it almost there, make another branch in case it goes sideways. The biggest issue with developing like this is that you are not a coder anymore; you are a puppet master of a very smart and sometimes totally confused brain.