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Source: https://writers.stackexchange.com/a/26280
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

Source: https://writers.stackexchange.com/a/26280
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

There is not one answer, as others have said. But I would suggest the following:

1. How many rewrites it takes to make a competent writer is a very different question from how many rewrites it takes for a competent writer to write a new book. Writing is a difficult craft and you should expect to have to do a lot of rewriting before you get good at it. That might mean rewriting the first book 20 times before you are good enough to make it good, or it could mean rewriting four books 5 times each before the fourth one is good. 

2. You should rewrite if you can see something wrong with a book and a way to make it better. Once you can't make it better, give it to someone else to read and listen to what they tell you is wrong with it (but not how they tell you to fix it). If you can now see what is wrong with it and a way to fix it, repeat the process. Once you can't see how to make it better, no matter what your beta readers say (good or bad), submit it. Or, if you still feel it is not good enough to submit, but can't tell how to make it better, stick it in a drawer and take it out next year.

3. A book can fail at multiple levels. Story problems cannot be fixed by fiddling with the prose. In fact, fiddling with the prose seldom fixes anything (which is why you should ignore all the suggestions from your beta readers). Good storytelling is about how the arc of the story works out and whether it maintains tension and provides a satisfying release. It is about how you set up the reader's expectations and how you pay off those expectations. Some writers spend countless rewrites trying to fix failures of tension or excitement with more and more overwrought prose when the real problem is that the events are simply not set up properly to create tension or excitement. Recasting the story is usually what makes a book work, no rewriting the prose. 

Original score: 0