So I never found out why this broke in the first place, but I did find a solution that forces the proper url to work
add_action( 'init', 'add_mypage_rule' );
function add_mypage_rule(){
add_rewrite_rule('^item/([^/]*)/?','index.php?pagename=item','top');
}
Sussed out from here:
https://stackoverflow.com/questions/18713230/wordpress-url-rewriting-parameters-in-url