To be fair, gear has never been more meaningless as an indication of someone's skill than now. With the advent of priority HM ops, it's extremely easy to get top end gear just by running EV/KP ad nauseam. I've been in quite a handful of operations where you can see players in full 224 hit enrage timers on every boss and get out-dps'd by formidable players in old 198s.
But I agree, if they want to do any harder content, what your friend's guild needs in the first place is not knowledge of HM mechanics, but gearing, learning and practising their rotations.