How to have WP Search widget index dynamically generated content?

Are families a custom post type?
If so, they won’t be included in the default WP search.
Try adding this to your theme’s functions.php

function lauren_include_post_types_in_search($query) {
    if(is_search()) {
        $post_types = get_post_types(array('public' => true, 'exclude_from_search' => false), 'objects');
        $searchable_types = array();
        if($post_types) {
            foreach( $post_types as $type) {
                $searchable_types[] = $type->name;
            }
        }
        $query->set('post_type', $searchable_types);
    }
    return $query;
}
add_action('pre_get_posts', 'lauren_include_post_types_in_search');