Gaming this is totally a crapshoot. Even with perfect information about weather on the day of travel and actual load numbers, you could not calculate with reasonable certainty even a probability of this working out. Even if you could, it's only a probability and a bunch of last minute misconnects could throw your careful calculations off.
VDBs are nice when they happen, but the odds are always with the house which, in this case, Delta and all their internal data.
Last flight tonight is at 807 pm on a 763.