Dining plan or not at Disney

I would say it depends on when you go. We have only been to Disney once but it was during the busy season and we did not purchase a dining plan. We could not eat in the parks because everything was book by the meal plan people. So it was vendor snacks until we got back to the hotel at nights.

Out of pocket and carry plenty of snacks to fill in. Carry your own water if possible.

Take or rent a stroller for sure. Make it a double. Carry back backs and kids that can fit in it.

If it is in the budget the Hoop De Do Review is a fun family show at the campground.

I would say not and pay out of pocket. We typically go in the fall when we can snag a free dining offer, but that I believe never applies to Fort Wilderness.

I know we never go away hungry and we could even split meals at times too. You get desserts which honestly we would never order if we were paying out of pocket as we are typically full.

Bottom line is if you order what you like and not the most expensive item on the menu, split meals, forgo desserts, you will come out money ahead paying out of pocket.

But.... If you are doing a lot of character meals which are typically buffets, it may be closer.

Here is a Disney dining plan calculator that may be helpful as well.
http://www.distripplanner.com/