Pardon a possible stupid question, but if I rent points for a hotel stay, and they offer Free dining for the off season, could I qualify? Thanks in advance!
You could stay at a DVC resort, pay full rate for the room through CRO, purchase a ticket and get free dining. Free dining is not available with any type of discount, including DVC points.
Or get a four or five night DVC stay on points, then make a separate cash/package reservation for the next three or four nights and get the free dining for that part of your stay.
If you rent a reservation from a member, you are not getting a reservation from Disney. Only from the member using their points.