The first time I went to DW, I really could not afford it. I was also stressing about menu prices. My oldest daughter, 13 at the time, gave me the best advice. She said it would ruin my vacation if I have to pull out my wallet for every meal, so we should get the meal plan. That's what I did. We had a great vacation. When we got back home, I compared the checks to the cost of the meal plan. It was a little more, but allowed me to relax, so well worth the difference.
I did not go again until 2013, this time with 2 grandchildren, mom and dad. could afford it this time, so pulling out the wallet every meal was not so painful. This saved me about $150 over the meal plan cost. Again we had a great time.
$150 can be the cost of a good TS meal, so no small amount in my mind.
I am neurotic about our finances, no doubt about it. So paying more for the dining plan than I could pay OOP did not make sense to me.
So I basically came up with my own "dining plan": (1) I went to the menu for each non-buffet ADR, picked out a likely meal for each person/group, added it all up, rounded up and added a 20% tip (2) added the buffet costs plus 20% tip (3) added approximate cost of two off-site meals and (4) added everything together. This did not take long to do.
That TOTAL amount plus $200 (for overages, snacks, small souvenir) was my dining plan cost. I allocated that amount to dining and suffering no anxiety when taking out the wallet, and I barely glanced at the bills. The total amount spent was actually less than I budgeted for.
I also allocated about 60-70 bucks for groceries (we either ate in our room at least once a day and brought food into the parks), but we'd have to spend that money at home anyway.
ETA specifics: So we were 2 adults, one child, one child under 3. Our trip was delayed because of weather so we were in Florida Monday to Friday morning. Day -1: McDonald's dinner while traveling. Day 1: off-site breakfast, takeout pizza lunch at hotel, dinner buffet ADR at Park Fare. Day 2: breakfast buffet ADR @ Crystal Palace, ice cream snack in park, lunch leftover pizza at hotel, dinner ADR @ BOG. Day 3: breakfast buffet ADR Akershaus, sandwich lunch at hotel; shared snack in park; dinner ADR Rose and Crown. Day 4: eggs/toast/fruit/cereal in hotel room, CS lunch at Yak and Yeti, dinner off-site BBQ joint. Day 5: quick breakfast at hotel, brought sandwiches to eat on plane. Total cost (including groceries) = $600. No skimping, just some budget-conscious decisions.
Notes: Buffets are cost effective if one or more person eats free (under 3); Alcohol: We had 1 beer/wine each at BOG and R&C and got bottle of rum from Publix for hotel room cocktails; Stroller - we snacked on water, granola bars, fruit, and string cheese we brought to parks; Full kitchen in hotel suite (key!); Don't order more than your family will eat - I ordered app instead of entree where applicable and it was plenty of food - you can always get more if necessary; If we hadn't left parks, we would have brought sandwiches in the stroller.