If you could delete half your house and re-build it at zero cost, it might be more valuable to just go for the first attempt and learn from it rather than trying to do everything in theory up front.
If you find yourself working on a "monstrosity" maybe you haven't seen the signs soon enough that you need to take a step back and refactor. But in my experience, at least starting on the problem with a POC gives you so much more high quality information that even if you have to scrap and re-write part way in, you're going to reach such a better result than if you try to map the whole thing out first without actually having tried to solve the problem.