My husband and I are both rare people (me more so than him), but we always find our meat a little OVERcooked in WDW. I'm not sure the servers and the chefs actually believe us, since most people are afraid of rare meat (we are pretty adventerous eaters...steak tartare and tuna tartare are big favorites), but we love it. With the exception of really fine restaurants, most places (not just in WDW) overcook their meat.
My suggestion is, if you really like medium, order medium rare, especially since the meat keeps cooking for a while after it comes off the grill.