I'm a Dis overplanner and I have been known to book ADRs before my package ressie was made, just to have the security of knowing that I can eat where I want. However, it made me sad last year to have to cancel all my hard-to-get ressies (Le Cellier Christmas Eve) when our trip failed to materialize.
On the other hand, our upcoming Mother-Daughter trip (July 17) was Disney-less until a month ago. I was lucky to get ressies for where we wanted at more or less the desirable times. Wanted to tweak them around, but there is no availability left for our favorites.