We got free dining for our first family trip that we had planned in February. We upgraded to the Deluxe plan because we wanted to go to a lot of character meals and I figured that if we had to eat, we might as well eat with Mickey & friends. I used a spreadsheet but you could do this on pen & paper. I made a list of 3 meals per day for every day we would be at WDW. I figured what days we'd be at which parks & made my ADRs for those days. We also had some interesting counter service planned. If also figured in snacks. Our tips would have been about $200- don't forget those tips! That trip didn't happen due to medical issues.
We went in April instead & decided to go with the regular dining plan. Due to increased crowds, I figured we'd have less time to spend at table service restaurants. We planned to pay OOP for breakfast each day, 3 additional table service restaurants, and extra snacks. We ended up not going to 2 of the additional table service restaurants we had planned and we didn't eat as many snacks as I thought.
Since we first came back from our trip, I was thinking that next time we would only do the QSDP since we had already done some of the character meals, but I don't think our next trip would be as fun without as many character dining experiences.
Here's what I will do to figure up what will be our best value: I will list all meals we will eat- 3 for each day we're at WDW & project snacks. I'll figure up what park we'll plan to be at for each day and schedule the ADRs we want based on that schedule. I'll look at menus & get prices for what I think we'll order. Don't forget to include tips. Then, I'll figure what we'll have to pay OOP for based on the 3 different dining plans. We'll choose the plan that is the best value based on cost and how many ADRs we want.
Just off the top of my head, I'm not sure I would pay out of pocket for the Deluxe plan. If I had free dining, I think it might be worth the price to upgrade just to ensure I wouldn't have to pay OOP for anything.
If you are leaving in 5 days, can you get a dining plan added? I thought it had to be over 1 week until your trip to add the plan. If you can add it, make sure you can get ADRs before you pick the regular or deluxe plan. You may have to pay OOP or choose the QSDP.