"I want to be as great as Steve Jobs, therefore I have to be as anal as he was about every last detail."

The problem with that line of thinking. (Besides the whole "Not iterating" thing.) Is that Jobs criticized others work. (Example: Wozniak built the AppleII really, Jobs just leaned over his shoulder to make sure he did it right.)

In the absence of a magic design compass like Jobs, you'll have to iterate and test to see if your changes are worthwhile.