I think it's possible to plan too much. On our five night cruise, I was worried that our rotation would have us missing Animator's Palate (first time) because that was the day we were in San Francisco and wanted to have dinner on shore. Fortunately, we were Triton's that night. But we had the pirate menu the other night we were in Triton's the other night so never got to experience their menu. Plus, whatever rotation you have, you may end up missing if you choose to eat in Palo's instead.
There is probably more flexibility for what guest services or the maitre'd can do for you once on the ship than through booking. My hunch is if you really wanted to switch one night from late to early, or to a different restaurant then your rotation, they would try to do so if its possible. When I missed getting waffles one morning at Parrot Cay one morning (apparently out, or too late), they sent someone to bring them for me from another restaurant. From what I've read, if there is a menu item you really want that isn't in your restaurant on your rotation, simply ask and they will try to make it work. Give the cast a chance to make your day and trust them to do their best, rather than overplan everything ( and believe me, I'm a planner).