IF.. post meta show... Conditional Tag Help...?

So, I would refactor this a bit:

<?php
$featured = ( has_post_thumbnail() ? get_post_thumbnail() : false );
$first_img = false;
$custom = false;

if ( ! $featured ) {
    // No featured image; look for attached images and get the first one
    $attachments = get_children( 'post_type=attachment&orderby=menu_order&post_mime_type=image&post_parent=".$post->ID ); 
    $first_img = ( $attachments ? wp_get_attachment_image_src($attachments[0]->ID, "thumbnail-size') : false );
    // No attached images; look for custom-field image
    if ( ! $first_img ) {
        $custom_meta = ( get_post_custom($post->ID) ? get_post_custom($post->ID) : false );
        $custom = ( isset( $custom_meta['custom_field_name'][0] ) ? $custom['custom_field_name'][0] : "false" );
    }
}
?>

So, now, you can just step through each source; e.g.:

<?php
if ( $featured ) {
    // Post has a featured image; do something with it
} else if ( $first_img ) {
    // Post has attached image; do something with the first one
} else if ( $custom ) {
    // Post has image attached via custom field; do something with it
} else {
    // Otherwise, there's no featured image,
    // no attached images, and no image 
    // defined in post custom meta. Do something.
}
?>

You just need to fit in your markup accordingly.

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