Having just finished my final Yeshiva exams, I wanted to share one essay that struck me as being very appropriate.
Why did G-D prohibit Moses from entering the Land of Isra'el?
When the Children of Isra'el demand water, G-D instructs Moshe to speak to the rock. In his anger, Moshe struck the rock, twice. Based on earlier Rabbinic commentary, Dr. Jacob Milgrom suggests that the sin is not the striking, but the statement, "Shall we get water for you out of this rock?" Thus the sin was tied to his implying he and Aaron, not G-D, were responsible for the miracle. Rabbi Kula suggests that it was the incident with the ten spies that caused Moshe to not be allowed to enter. This is due to G-D declaring only Caleb & Joshua would enter, excluding even Moshe.
Both explanations above have merit. There is a third explanation postulated by some Messianics and Christians. This explanation bases G-D's anger on the first striking of the rock being a shadow of Messiah's first incarnation, and speaking to the rock was to have been a shadow of His return as King of Kings. Thus, Moshe was punished so severely due, not only to his disobedience but, to it's ramifications for the future prophetic significance.
As to which explanation is correct, it is unwise to be dogmatic. One or a combination of all may be correct. What is clear is that, due to either his own disobedience, or the disobedience of Isra'el, or both, Moshe was not allowed into the Promised Land. There is an additional thought that might be worth consideration. Is it possible that G-D, in His wisdom, decided Moshe entering the land would not be wise? It is believed G-D hid the spot of Moshe's burial to prevent the Israelis from making it a place of worship. Could this be part of the reason G-D chose to not allow Moshe into the Land? Could G-D have prevented Moshe from entering the Land because the people would turn Moshe into a "god", or lose site of the One True G-D?
Shalom - Rabbi Gavri'el