We have been lucky enough to get free dining in one form or another for at least the last 10 years or so. (Bounce backs, special offers etc). We are a family of 4 that averages 10-14 day trips. We usually tally up our receipts even with the free dining, and average anywhere from $1800-$2800 in food. For us, free dining beats a room discount every single time. We can vary our resort type, but stay mod more than anything. Even at full rack rate on a room, let's say an average of even $200 per night, which was high for many past trips, more like $160-$180, we would only have saved $50 a day with even a 25% room discount. On a 10 day\9 night trip that's $500. Heck, we spend a minimum of $150 a day even with a counter service plan!
Honestly, if you can get the dates, and are more than two people, I think it's well worth it.