We just got back from our first trip ever last month. We had missed the
free dining plan last year when we booked by a couple weeks

We are planning our next trip and thinking September. I heard this was "normally" when they have the free dining. Any tips on booking and trying to add it or waiting it out and seeing if the rates go up etc? Also, last time we stayed at a value resort and had the regular dining plan
its my understanding that we would only get the quick service dining plan for a value resort, right? So if we want the regular dining plan with table service meals we would need to stay at a moderate resort this time? Any advice on picking a moderate resort if we need to that is relatively inexpensive for 2 adults, 2 kids and a 2 yr old?
Also, I am new to this board and still pretty new to Disney so sorry in advance if I don't know something obvious or need to post this in another area of the board.