Well I will start by giving you some food for thought.
Would you want to do one sit down meal per day for the full 2 weeks you are there? You would be paying for the dining plan if you go in April so you need to consider whether it would be worth it for you, based on what you think you would be eating. Not as hard as it sounds. The basic dining plan gives you one quick service meal per day plus one sit down (table service) meal per day and a snack.
Let's just look at the Table Service (TS) for now, since you are thinking character meals at this point. This includes a main course or full buffet/all you can eat family style meal, plus one non alcoholic beverage and a dessert. You also get your quick service (CS) meal which includes an entree or combo meal, dessert and a beverage. I can look at that and tell you immediately that I will not eat dessert twice a day, neither do I want to be tied to a restaurant reservation at a certain place and time every night. For me it is too restrictive. For many people, it is part of the experience and adds structure to the day so what works for one person is not necessarily going to be the answer for the next.
I think a good starting point for you would be to go onto allears.net and have a look at the menus, take a typical day and try and figure out the kind of thing you would be likely to order during the course of that day. You need to add tax onto the prices (dining plan includes tax) and also 18% to your TS meals for tip. Then take the cost of the dining plan for all five of you for that day and see how the figures compare.
I like to do a few character meals but don't like to be tied to all those reservations for 2 weeks. I have done QSDP and paid out of pocket for my few character meals and it was cheaper for me that way. I have also done no dining plan and paid out of pocket for all my food and still saved on getting the dining plan, however if you enjoy nice restaurants, want to try a few signature meals and plan on eating a good sit down dinner at least 10 out of your 14 nights/days and maybe double up for a few signatures to free up some evenings (signature meals use 2 TS credits per person) then the dining plan may very well save you a fair amount of cash.
Keep talking. It takes a bit of work, a lot of patience and a calculator, but you get there eventually.
