How come Ahron Hakohen didn't pray to enter E"Y like moshe did? Did he have less of a desire to enter?
Rashi explains in the beginng of פרשת ואתחנן, that Moshe only prayed to enter eretz yisroel after he entered the land of sichon, which was part of עבר הידרן that would be considered eretz yisroel. He reckoned that if Hashem let him go there, perhaps Hashem annulled his decree of not entering E"Y, and (putting in the interpretation of the sifsei chachamim) with prayer, perhaps Hashem would let him enter eretz yisroel proper.
This is why Moshe prayed to enter E"Y. Aharon, was niftar in parshas Chukas prior to Klal Yisroel entering עבר הירדן, and never considered that perhaps Hashem annulled his decree (Bamidbar 20,12) of not entering E"Y.
The Toldos Yitzchak (Rabbi Yitzchak Karo) offers two answers:
- Moshe's purpose to enter E"Y was in order to fulfill the mitzvos התלויות בארץ.Because Ahron (being a Kohen) was to gain from those, as the Kohanim get many of the products of these Mitzvos (Teruma, Challa...), Ahron was afraid that people will say that he only wants to enter E"Y for that purpose.
- Moshe wasn't zoche that his children should succeed him as leaders of Klal Yisroel so he wanted to enter. Ahron's children , on the other hand, succeeded him with the Kehuna which sufficed for him.