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A workaround by extending the WP_Image_Editor_GD class

The problem is how to access the image sizes before we change the quality of intermediate jpeg images.

Note that the image_resize() function is deprecated.

We can use the jpeg_quality filter from the public get_quality method of the abstract WP_Image_Editor class:

$quality = apply_filters( 'jpeg_quality', $quality, 'image_resize' );

or the wp_editor_set_quality filter.

Here's one idea how to set the image quality based on the image size (width/height):

/**
 * Set image (jpg) quality based on the image size (width/height)
 * @see http://wordpress.stackexchange.com/a/165241/26350
 */
add_filter( 'wpse_make_image_arguments', function( $arguments, $filename, $size, $function ) 
{   
    // Only target jpeg cases, i.e. with the quality set in $arguments[2]       
    if( ! isset( $size['height'] ) || ! isset( $size['width'] ) || ! isset( $arguments[2] ) )
        return $arguments;
        
    // Modify this part to your needs:
    if( $size['height'] <= 150  && $size['width'] <= 150 )
        $arguments[2] = 2; // very low quality for easy testing
   
    return $arguments;
}, 10, 4 );

where we've extended the WP_Image_Editor_GD class:

/**
 * Extend the WP_Image_Editor_GD to add the custom wpse_make_image_arguments filter.
 * @see http://wordpress.stackexchange.com/a/165241/26350
 */
add_filter( 'wp_image_editors', function( $editors ) {
    // Note that the WP_Image_Editor_GD and WP_Image_Editor_Imagick classes
    // are included within this filter. So let's do the same for our extension class.

    // Our extended class:
    class WPSE_Image_Editor_GD extends WP_Image_Editor_GD
    {
        protected function make_image( $filename, $function, $arguments ) {
            // Add a custom filter:             
            $arguments = apply_filters( 'wpse_make_image_arguments', $arguments, $filename, $this->size, $function );

            // Parent method
            return parent::make_image( $filename, $function, $arguments );
        }
    }

    // Prepend the extended class to the array of image editors:    
    array_unshift( $editors, 'WPSE_Image_Editor_GD' );

    return $editors;
} );

where we introduced the custom wpse_make_image_arguments filter.

This way we can modify the quality settings, before the intermediate files are saved.

Here's an example:

PS: I didn't check out the case when the Imagick library is used instead, but I guess we could do something similar by extending the WP_Image_Editor_Imagick class.