When DH and I take our solo trips, we always upgrade to the
DDP when we stay value during
free dining.
2 adults staying at POP with free QS for 6 days/5 nights is $1250, upgrade to DDP and the cost is $1430 so only $180 difference. Upgrading to CSR to get the DDP for the same trip is $1787 which is an additional $357 over the DDP at POP. Now, we could go to CB for $1618 which is just an additional $188 over the price for the DDP.
NOW I will say that when we go and take our grandkids, we do not upgrade. It is just to hard to work around reservations with kids. Having to stop what you are doing in the park to get to a ressie can be time consuming. They ask you to check in for your ressie 15 min ahead and then another hour+ for dinner. The kids just want to be in the park (or at least that has been our experience)
Truly we love POP, it really gives you the Disney feeling being there. We aren't fancy people and we aren't in the room enough to justify the additional cost. Plus with AoA just across the lake it is fun to go over there and emerse yourself in the giant movie sets. We have stayed at POP our past 7 trips, prior to that we have stayed at CBR, CSR, ASsp, ASmo. We have not ever stayed anything above moderate. POP is our Disney home away from home and it has always been a great experience for us whether we take our grandkids or it's just the 2 of us!
Some of our favorite ressies on the DDP normally include:
O'hana- our favorite!!! We always do this on our MK day so we can jump on the monorail and get over there and back pretty easily.
Le Cellier - we only use 1 persons DDP (so 2 credits) since my favorite thing on their menu was the spicy chicken sausage appitizer and now they have taken it off the menu-not sure if we will do Le Cellier again

. Before my DH would eat a steak with the DDP and I would pay OOP for my appitizer.
Teppan Edo- DH likes this more than I do since we have a hibachi grill locally that we can go to.
Sci-Fi- WE LOVE THIS PLACE for burgers and onion rings

Tusker House for Breakfast - DH loves this breakfast (i dont think I get my moneys worth) It is great for kids.
Yak and Yeti- only been once and it was yummy.
We also like Whispering Canyon but havent been in a couple of years, Boma but the flavors are a little bit to much for my DH.
We really want to try during our next trip: Via Napoli, and we may have to find a new steak house