We have only ever booked during free dining after it's been released. It's the main way to convince my husband to go. We both enjoy the "all inclusive" feeling of it. We usually stay moderate. He doesn't feel bad ordering steak and we don't feel bad not finishing our meals when we are full. It's also a treat to get dessert. I like not coming home with a huge credit card bill with the vacation food on it. That being said I would never pay for it ( I know we kinda pay for it with rake room and park hoppers but we go during value season and want hoppers anyways). One problem with depending of free dining is sometimes you are already well within your ADR booking window before they even announce it. If I was you I'd look at historical past free dining times, book your vacation during these times and make ADRS assuming you will get it. ( if you have flexibility enough to do so) If they don't release it then cut back on some of the dining you aren't really passionate about. The dining plan really gives you more food than you need. Also if you have never looked into it before it may be worth looking at the placing you were hoping to eat in the dining plan brochure. Some more popular places or fancier places are 2 credits which may change your mind.