If you realize that's what must be done, it must be done. There's no reason to send out a story that's not the strongest you can make it; even if it gets published, do you truly -- as a writer -- want to have that feeling of, "boy, there's so much I should've fixed"?

I've rewritten my current WiP a total of three times so far. It's two different protags, so it's really two stories that don't blend until the halfway point. The first rewrite, I completely redid one protag's story, which mean totally rewriting the second half of the book. The second rewrite, I redid the other protag's story, and again with the rewriting. Then I realized what was wrong with the second half of the book, and had to rewrite that, a third time. And then I realized: the two protag-stories are no longer truly seamless because I've rewritten them separately, and now I need major revision to make them as smooth as they'd been in the first draft. Ugh!

What makes me feel like less of a dork for all that is recalling Holly Black's comments in her afterwords for Tithe: that she'd rewritten the book, from scratch, a total of seven times before it became the version now published. So I say: three or four times? That's clearly nothing, if that's what it takes to learn the story and find the words it needs.