I did play around today looking 60 days out to simulate my experience, for closer to my actual trip (Nov). I found using the My Disney Experience app better than using the desktop browser and to let it search all dining at various park for each day , and yes I tried the suggestion to enter specific times rather than "lunch" or "dinner" and had some success. Though the choices that came up weren't the most exciting there were still several options per park avail...so worst case we sit-down SOMEWHERE which is still a win.
I think the ones that are of most interest (and probably the hardest to get):
MK - Cinderella castle, Be Our Guest
Epcot - Space 220, San Angel Inn
Hollywood Studios - dinner package with seats for fantasmic
AK- unknown???
Character breakfast - Chef Mickeys at contemporary
We have 2 off days with nothing scheduled so for those if I get T-rex at DS, Toothsome at UNI, and a decent character breakfast anywhere I'll be happy. If we then end up at vanilla places that happen to be avail in the 4 main park days, so be it, and maybe for the better.
Any other suggestions that have theming the kids would enjoy (ages 6, 7, 10)?