We're also FL resident AP holders and we love the
DDP.
The
FREE dining question is an academic discussion because registration for free dining is over.
I'd say to take a look at the restaurants covered, with special attention to which ones are a single TS and which require two.
For those which require only one TS (and that's most of them), my math is pretty straightforward. DDP is $37.99 per day per adult, and that price includes tax and tip. I can't eat dinner in most WS TS restaurants for that price including tax and tip, so I figure I pay $37.99 inclusive for dinner and all my CSs and snacks are free bonus items.
I did an analysis of our May trip on DDP, comparing NOT to the menu prices of an appetizer, entree, and dessert, but to what we
really would have ordered if we'd been paying cash with our 20% DDE discount. Even comparing it that way, we saved $70 in a five-night trip and all the CS and snacks were free. If I'd counted the CS and snacks, we'd have saved several hundred bucks.
Your math will vary greatly depending on the composition of your family and your dining habits. But even worst-case, if ALL of your party are adults and you typically eat a nice dinner each night, you'll come out ahead with DDP unless you're eating at 2 TS places.