ADR's and reservations are 2 completely different intenties. Local residents can make ADR's without ever staying at disney...so disconnect the 2 in your mind.
DDP-you are 80% sure that you will be on the dining plan(tell the agent that you are on the DDP)free or not it does not matter.
Rooms- all hotels only have a limited # of rooms that will be given
free dining(so it is important to book early...for your best choice of hotel).
Classification of hotels...
Value WDW style is a really nice Value hotel you would find in your city...like Super 8, Howard Johnson, etc...
Moderate WDW style is a really nice version of a moderate hotel you would find in your city like a Hampton Inn, Ramada etc
SO would staying in a "really nice" version of a Howard Johnson's be upsetting to you...It wouldn't bother me, because like you say- you are not in your room most of the time. I like a pool, I like lots of dining, and a clean place to sleep. But I am staying at the Poly

because it's free dining, so I am upgrading to a better room(usually we are in DVC or once in a while a Moderate)
Now regaurding you CIndy's quest...In your case I think I would use
Dreams Unlimited...make your ressie(even if it is at full price-you can always go for other room discounts) and have them secure your ADR's at the 180 +10 days. You can also be trying on your own...but this way you have a shot. Adr's can always be cancelled if you end up with too many. DU will then try to get you the free dining when that becomes available(or what ever discount becomes available R/O,
AAA, AP-that you can qualify for), they will apply the codes to your reservations.
Remember the 2 are seperate, they may ask if you are staying on site or using the DP...but that is more for marketing information...you can always call and adjust your ADR to reflect that you are on the DP etc once you have secured your ideal reservations.
Good luck!!