If there is availability and your dates/resort/resort category qualifies. It is best to be flexible because you might have to change to different dates, resort, and/or resort room category to qualify. Also, the rooms allocated to free dining come from a different inventory so your current reservation would be cancelled and a new reservation under the free dining promo would have to be booked.
Having a package booked in advance will not help if free dining is a must. If you are planning to go regardless of whether or not you get free dining, then booking early is better so that you will get the room you want.
Also, the rooms allocated to free dining come from a different inventory so your current reservation would be cancelled and a new reservation under the free dining promo would have to be booked.
Your existing package can be modified to a free dine package if you find availability, keeping the same deposit and using the same confirmation number. You are right that having something booked won't give you any advantage when looking at free dine availability.
If you have an existing room-only reservation, that would have to be cancelled, your deposit refunded, and a new package booked with a new deposit taken.
Remember also that you can only have one discount applied to your reservation at a time. If you have some room-only discount, for example, you'd have to give that up to get the free dining package.
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