My plans weren't so much trying to sidestep the system as it was to pay what I consider to be a fair price to what was ordered and eaten. For arguments sake, take the free out of the dining plan for a moment. Our family with DS11 and DD8 were going to go to WDW this late August-early September regardless, and were planning to book with the dining option. DS qualified as an adult and would be charged $35/day as would my wife and I. Ds is an extremely picky and light eater. This being the case why should I expect him to order off the adult menu, and with an appetizer and dessert to boot. The food would just go to waste.
My plan was to pay OOP for DS and have him order off the child's menu along with DD. Then we would use the saved TS credits to use towards a Signature dining experience. Why should this be wrong? Wouldn't I have been paying the adult price, and thus be entitled to use it for an adult purpose.
It just so happens to just prior to booking our trip through our TA that Disney came out with the
free dining offer. Why should this change anything. Just IMHO.
Now I figure to do what I want to do, I will feed DS at a counter service place so he can have his burger, or chicken fingers, PBJ, etc., and then he goes in with us to the restaurant of our choice and while DW, DD, and I order our regular meals he can just drink my non-alcoholic beverage and have a dessert . I don't feel by doing this we would be keeping the table from someone waiting to eat as we would not be lingering over just coffee and dessert.