DVC reservations are not MYW packages and you can't make one into a MYW package. The two reservation systems, DVC and CRO (Disney's Central Reservations Office) are completely separate.
Disney has, however, arranged that DVC members booking through Member Services may purchase the dining plans with their reservations.
If you do the rental, you'll be buying your tickets separately, not as a package, and you are not eligible for free dining. You can, however, have the member you are renting from add a dining plan to your reservation. Rules are similar - everyone registered in the room must be on the same plan for the duration of the stay. It's possible with DVC to segment the reservation, stay in the same room and only get dining for part of the stay, discuss that with the member you rent from if it interests you.
The member must add the DDP to the reservation and pay Member Services for it. You won't be able to do it because DVC Member Services will only deal with the actual member. You'll need to arrange with the member how you will pay for the dining plan. It must be paid when it is added to the reservation, and it must be added no later than 2 days before arrival.