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Does iPhoto do lossless JPEG cropping?
This is my experience also. I saved a raw image as 90% JPEG, and there was noticeable (when looking at the pixel-level) quality loss. Then I repeated 20 times saving the previous JPEG as a new 90% JPEG. The final JPEG had extremely little change compared to the original JPEG, and far less quality loss than saving as JPEG in the first place. So to conclude, if you start saving as JPEG anyway, then don't worry about resaving in the same quality level.