We've had great success sharing meals at many of the places you plan to eat at- Citrico's, Kona, Via Napoli, LTT, Le Cellier, and Cali Grill. We weren't on the DDP, but I don't see why it would matter. The only thing you might encounter is if everyone wants a soft drink you might have to pay for one extra drink. We always share the Big Kahuna breakfast platter at Kona. At Citricos we shared the grouper and they split it for us in the kitchen. Also we shared the pork at Cali Grill and it was split by the kitchen. My son and I have shared the burger at Le Cellier and LTT. We usually like to order an appy and dessert so splitting meals works well for us to try more things. I really hope it works out for you. BTW, I love your Eyeore rating system. So cute.