Adding inline help to category/taxonomy checkboxes in admin sidebar

This is an adaption of an answer by /user/gmazzap so there may be better way to go about it. Either way, I got it to work.

Pretty much you would filter the checklist arguments and pass in a new Walker Class which you can then define what happens at the start of the list start_lvl(). At that point you should be able to pass any HTML you need to. You should test this in a few cases just to make sure it works in the scenario(s) you need it to. Also note that there’s a taxonomy limit on the conditional in taxonomy_checklist_desc() so that it only shows in category but you can remove this to apply to all taxonomies or add more taxonomies if need be.

/**
 * Add Description To Taxonomy Term Checklist Metabox
 * @param array $args
 * @return array $args
 */
function taxonomy_checklist_desc( $args ) {
  if (
    ! empty( $args['taxonomy'] )
    && ( $args['taxonomy'] === 'category' ) // only for 'category' taxonomy
    && ( ! isset( $args['walker'] ) || ! $args['walker'] instanceof Walker )
  ) {
    $args['walker'] = get_Walker_Tax_Meta_Desc();
  }
  return $args;
}

function get_Walker_Tax_Meta_Desc() {

    class Walker_Tax_Meta_Desc extends Walker_Category_Checklist {

        function start_lvl( &$output, $depth = 0, $args = array() ) {
          ?>
            <a href="http://i.imgur.com/eu6xBup.jpg"><em>This is where I'd put my description... IF I HAD ONE!</em></a>
          <?php
            parent::start_lvl( $output, $depth = 0, $args );
        }

    }
    return new Walker_Tax_Meta_Desc;
}
add_filter( 'wp_terms_checklist_args', 'taxonomy_checklist_desc' );