Nothing has to be paid first--you don't even have to have a hotel reservation. The rule is 180 days, or 180+10 days if you have a resort reservation in place.
If you're going down for
free dining, you're already within the window so get on that phone! Le Cellier is already booking up for dinner! Call now! Free dining ain't nothin' if you can't get into your favorite restaurants!
OT: Great line you might enjoy from a "They Might Be Giants" song: "You're older now than you've ever been, you're older now than you've ever been. And now you're older still." Sigh. Too true, too true.
Edited to add: OMG! LOVE your family pirate photo! So cute!