The Midrash enumerates 10 phraseologies of prayer bur incredibly what is the most common term, תפלה, is left out, how? The Sfas Emes (5631) explains that the 10 terms are not different modes of prayer but rather are 10 ways how one readies themselves to pray and then one can come to the actual act of תפילה.
Rashi says that tzaddikim like Moshe could ask for their requests to be granted due to the great merits but instead they ask Hashem to grant their request not as a reward, but as a free gift. If they are deserving of the request why do they even need to ask? The Sfas Emes explains that Rashi is not referring to being deserving of the request being granted, he is talking about the first step of prayer, the right to even ask Hashem, but the request itself is not deserved.
The Midrash says סימן לתפלה אם כוון אדם לבו לתפלה. Asks the Sfas Emes, how is כונה merely a סימן for tefillah, it is the defining characteristic? He explains that it is not to be taken for granted that one can just pray before Hashem, to be prepared to pray also is something granted from Hashem and the siman that one was prepared is if one was able to have כונה in their prayer.
The Sfas Emes adds the impetus for prayer is the request, לאדם מערכי לב, the request is why one turned to Hashem, but once one is engaged in the act of tefillah, one loses themselves in the connection that occurs and the request is no longer a concern and would be forgotten if not for the fact that Hashem puts it into the person's mouth, ומה' מענה לשון. That is the double terminology, ואתחנן ... לאמר. The word ואתחנן is in the reflexive form, a person starts out becoming "prayed," in other words, the ability to pray to stand in prayer before Hashem, and then לאמר, he can engage in the actual prayer.
It is noted that the gematria of תפילה and שירה both are 515 as is ואתחנן which is the number of prayers Moshe said. Indicating the nth degree of prayer is that of שירה (see Baal HaTurim.) In other words, as the Sfas Emes teaches us, although the request is the starting point of the prayer, the prayer itslef it one of praise and appreciation of Hashem.
The Bach (siman 208) says there is holiness to the fruit of Eretz Yisrael itself. The Eliya Rabbah objects based upon the Gemarah Sotah (14a) that wonders why would Moshe care to eat the fruits of Eretz Yisrael and instead explains Moshe's great desire was to fulfill the mitzvot of the land. If there is a unique holiness to the fruits of the land, maybe that is what Moshe desired? The Meshech Chachma asks why did the Gemarah not say he wanted the mitzvah of yishuv Eretz Yisrael? He says it must be the areas in control by Reuvain and Gad had the sanctity of EY do that mitzvah Mosh already fulfilled. In light of this it is possible that the kedusha of the fruits Moshe already had as well and all he was lacking was the mitzvot that apply only after settling and dividing up EY. If the Mesech Chachma is right however, so why was Moshe withheld from entering the land? Rashi says that Moshe thought the neder that he was not allowed to enter was nullified by his living in the lands of Reuvain and Gad, but Moshe's request is still refused indicating that the Transjordan land is not the same as EY?
