Free dining is a great deal at the value and moderate levels; room discounts are usually a better deal if you stay deluxe. Obviously, you also need to enjoy Disney's restaurants as well. No amount of free food is a good deal if you don't enjoy it (and I completely respect those who feel like free dining was the demise of Disney restaurants. I just don't happen to agree with it. We've had many, many wonderful meals at Disney over the last couple of years.)
I'm a DVC member, but I'm also a single mom. Love the space of the villas, but I don't generally do any real cooking to speak of (if I did, it wouldn't be much of a vacation for me.) We really DO enjoy the Disney restaurants. The TiW card I have is great and gives us the flexibility to order exactly what we want rather than be tied into ordering a specific way. Also, my kids are now 10 and 13 and adults in Disney's eyes. Paying for the dining plan for the 3 of us costs $138 a day.
All that being said, I still booked a Memories package for us over Labor Day weekend. We travel to Disney 3-4 times a year and I haven't done a Photo Book since our first visit over 2 years ago; so I don't mind that it's included in the package (even if I'm paying a little extra.) At CSR, the room only rate, even at rack prices averages out to $169 a night. Subtract out the cost of dining, and it's like paying $31 night for the room. If I had another person with us, it would be a wash. Now it's no 1BR villa, but it will not be unbearable for me and 2 kids for a long weekend. And, since we aren't planning on renewing our AP's after they expire in September, I can easily put the 2 day park passes to good use on our next trip. And the best bonus for me, was that I also booked my flights thru Disney and it was over $100 cheaper than what I've been paying on average for the last few years (on my favorite airline, to boot!). Overall, it was a win/win situation for me and I'm really looking forward to trying out a new resort.
I think many of the people who gripe about free dining fall under one of the following 3 categories:
1) People whose dates conflict with the free dining offer who can't take advantage of it.
2) People who stay deluxe - it's simply not that great of a deal.
3) Certain DVC members. I understand this to an extent. We are so loyal to Disney that we spent enormous amounts of money up front for our lodging and return year after year and spend a lot more money once we get there. I know our rooms are significantly discounted and don't think we deserve free dining but it sure would be nice if we could a discounted price on the dining plan. I'd even be happy with a discount on park tickets other than AP's. At the end of the day, though, I realized that free dining was mine for the taking if I could forego a villa for one trip. So no sour grapes here. I'm even toying with renting out my next planned DVC stay and using the money to book another free dining trip.