Budget has usually dictated our resort choices. When we were a family of 6, with the youngest under 3, a room at POR with the trundle bed was the least expensive on-site option. After our youngest turned 3 (and when we had my mom and sister with us on parts of earlier trips), 2 rooms at a value was our least expensive option.
On our last trip, we were a party of 10, staying for 2 weeks. As much as I enjoy staying on-site, we just couldn't pass up the incredible savings of renting a pool home. We spent $2100 for 2 weeks for all 10 of us, when 3 rooms at a value would have been double that.
We are a family of 7 now, so even though I would love to try all the deluxe resorts, even if we could afford it, I don't think I could justify spending $500 or more per night for our hotel. That's just crazy to me. Even staying at a value resort at $200 per night is hard to sell to DW when we can have a large home with our own private pool for $150/night or less.
That's why I'm on this thread.

With our large family trying to stay on a budget,
free dining is the only way I can convince DW it's worth it to stay on-site.