OP, in your case, I think it would be a better deal to upgrade to a moderate to get the regular dining plan.
Some folks on here have given you good advice regarding cost comparison. In my view, the best use of
free dining is families with children 10 and over who do character and buffet dining as their TS. Then eat a regular QS at a park every day, with your snack for breakfast, or OOP for something quick.
2 adults who like to drink and get apps, or families with little kids usually will make out better with a room discount. Upgrading to TS plan from QS will cost around $20 a person - could you upgrade your room for an additional $80, get a better resort and the regular dining plan? If so, then it's a good idea.
The question to ask yourself is would you eat that way anyway? If you would eat at a TS every day and only pay tips, nothing extra off the menu, then you're golden.
We had a TIW, staying at OKW one year, and went over to POFQ for a QS dinner (since we got the discount on our bill). We saw many people who had their receipts from dinner going to get dessert on their way back from parks. So apparently the dinner and dessert from your resort food court might be able to be spread out and you can get that dessert as your evening snack. Otherwise, you get big handfuls of Mickey Rice Krispy bars on a stick because you're too full to eat dessert right away.
We were hoping for free dining for this year's trip because we do plan to eat out most days. But a room only discount will probably be better in the long run. We'll eat some meals in our cabin, eat less when we go out and generally feel better and not overloaded with food. I don't want to be tied to constant reservations and running from one place to another, I want to be more free with our time.
Anyway, hope that helps. And I hope this thread doesn't turn into a debate like so many of them do.