Free dining requires a room package at full price and including 2 day tickets. If you look at the full price of the rooms, you are better off using points and purchasing the dining plan or paying out of pocket. For September, studios start at around $315 plus tax (OKW), BLT is $415 plus tax. Pay that and buy tickets and you can get "free" dining.
Just for fun I priced a stay at Old Key West in a two Bedroom for eight nights with the "free dining" special. (August 25 - September 2) With a 6 day Magic Your Way Base ticket, the two bedroom and the "free dining" the price is $7016.82
It's worth it for the concierge access. Not worth it for the view. There are five two bedroom lockoffs - three savanna with the view partially blocked by the roof overhang and two pool view. At least one of the one bedrooms on the savanna side is handicap accessible.