Oh my, I was kind of hoping no one would ask. You'll probably be sorry you did...but here goes:
I'm not sorry at all and I completely understand your frustration.
Just for the record, I don't think "free dining" is "free", it's just another discount in my mind which is why I always throw quotes around it.
First, it's usually only a better deal if you're staying at a value, and then it is a reduced plan.
Not true, it's really a great discount for value and moderate resorts but not so much for deluxe resorts. The last "free dining" program was offered through the fall, regular and holiday seasons. The fall season rack rate for a value was $111 and the room-only discount was (I think) 20% which a savings of $25 including tax savings. I look at it this way, everyone needs to eat at WDW. The difference between rack rate "free dining" and the room-only discount is $25. Could YOU feed your family on $25 per day? Now, if you're looking at the holiday season, the rack rate is $199 (!) so the room only discount would be $45 less than "free dining", but again ... could you feed your family on $45 per day at WDW? I know I can't and we rarely eat at TS restaurants.
Moderate resorts are more expensive and the room-only discount is better. But so is the dining plan. A moderate in fall season is $204 with a room-only discount of 30%. That's a savings of $69. I don't know about you but I can't leave a single TS restaurant for two people for less than $70. Looking at the holiday season, rack rate is $285 (!!) and room-only savings is $96. For our family of 3 Disney Adults, that's probably where I would think hard about it. IF we wanted a TS every night it would be worth it since we average over $100 per TS meal.
But still, pay $100 you get a room and some food for up to 4 people. No matter, we wouldn't touch a free dining discount no matter how good the deal. It's a pia and it turns your vacation into nothing but planning meals and trying to figure out just how much you can manage to get. I see people all the time talking about what the most expensive thing on the menu is- not what they want to eat but what costs the most? Is crazy...
You're absolutely right! It is crazy. I hate all that planning. I hate the 120-day (plus 10!) ADR window. I hate that if I missed it (like I did for my December trip) I have to "stalk" the cancellation threads and MDX for an opening. I got both BOG and California Grill that way. I made FP+ reservations last night and I hated sitting there thinking, "OK. I *think* we might do EMH at the MK which is until 3:00 am. We'll get back to our resort at 4:00 am, asleep by 4:30, wake up groggy at 11:00 and we can be at AK by 1:00, but we have a BOG ADR at 7:05, so we can't spend too much time at AK so when do I have to schedule the Safari again?" It really hurts the brain sometimes to have to plan to that level. I have to admit that in pre-FP+ days we probably couldn't ride the safari if we got there at 1:00 but that would have been our choice since we stayed out late the night before. We would have made the best out of a relaxing day at AK without FPs.
FWIW, you are also absolutely right about the menus getting "dumbed down" due to the
DDP. We have moved away from Disney TS restaurants once my DD was a "Disney Adult" and the cost was crazy for her. We eat offsite a few times a visit now (I LOVE the whole Maine lobster special at the Old Town Ale House on Wednesdays!) because the food is (a) better and (b) cheaper.