Does anyone know of a source that discusses everyone's entering Israel at t'chiyas hamesim and the ban on Moshe's entering Israel in light of one another (and, preferably, attempts to reconcile them)?
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It's not really a contradiction. The ban wasn't everlasting (i.e. it didn't extend to the end of time and resurrection), but precluded Moshe Rabbeinu from entering Israel in his lifetime.
The Midrash Rabbah tells us that Moshe did not enter the land for the sake of the generation that died in the desert.
Midrash Rabbah V'Eschanan (words in brackets my addition):
The Or Hachayim on Devarim 33:21 brings this idea as well, and uses the phrase "to bring the generation of the desert into the World to Come".
Although it could be argued that both of those sources could technically be interpreted to mean that Moshe would bring them into Gan Eden (as opposed to into the land of Israel with the Resurrection), the Lev Chaim (Part 1, Chapter 32) quotes a Midrash Hane'elam that says explicitly that "Why did Moshe pass away outside the Land of Israel? To show the nations of the world, the same way G-d will resurrect Moshe, he will resurrect his whole generation, in the merit of their receiving of the Torah".