With your method it would be very tricky, if it’s possible at all. What you could do is use a custom header with flexible dimensions. That would allow the user to upload the header image and then crop it how ever they needed easily.
// Register Theme Features
function custom_theme_features() {
// Add theme support for Custom Header
$header_args = array(
'default-image' => 'http://example.com/image.png',
'width' => 0,
'height' => 0,
'flex-width' => true,
'flex-height' => true,
'random-default' => false,
'header-text' => false,
'default-text-color' => '',
'uploads' => true,
);
add_theme_support( 'custom-header', $header_args );
}
// Hook into the 'after_setup_theme' action
add_action( 'after_setup_theme', 'custom_theme_features' );
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