Best practice for compressing images to uniform size?

What would be an effective method of compressing all the images (JPEG) used by an application to a uniform contentLength?
Initial thought is to generate a new copy using processCopy with successively smaller integer values for compressionQuality (in steps of 5 or 10 say) until a result smaller than the target length is achieved, then replace the original with the first suitable copy.

contentLength is decided by many factors such as height, width, compressionQuality.
If all images have same height and width, changing compressionQuality will help to get expected contentLength. But be care when using too small compressionQuality, which may make image quality poor.
Another way to have uniform contentLength is using TIFF format with NONE compression.

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