Thank you for your response as to why Moses did not enter the Promised Land. I have considered that perhaps Moses didn't literally need to enter the new land because he had long ago "taken a stand" on "holy ground:" "And when the Lord saw that he turned aside to see, God called unto him out of the midst of the bush, and said, Moses, Moses. And he said, Here am I. And he said, Draw not nigh hither: put off thy shoes from off thy feet, for the place whereon thou standest is holy ground" (Ex. 3:4, 5). I wondered if you felt there is any validity in this thought.
We can almost imagine the scene. Moses was having a normal day tending his sheep, when suddenly he noticed a bush burning, but it was not consumed. He got up to look, maybe racing over to see it. When just as suddenly, God called him by name, and he responded, "Here am I." At that point, God told him to stop, not to come closer, and to take off his sandals because the very ground was holy.
It's impossible to know what Moses was feeling or thinking at that moment, but up to this point, there is no indication that he attached any religious significance to the moment. He ran over to see what was happening without any hesitation or compunction about doing so. God established the boundary: Don't come any closer. Moses was prevented from thoughtlessly intruding into the presence of God. God told him to remove his sandals, which was considered to be a sign of respect (much like a modern day person might take off a hat). God declared the place to be holy ground because of His presence. It was not intrinsically holy, nor did it remain holy past its purpose (for God to reveal Himself to Moses). Scholars don't have a clue where this place was. There are no ancient markers or pilgrimages to this spot, but then they can't identify Mount Horeb (site of the Ten Commandments) either, and the Israelites stayed there for months.
This situation is much like the one recorded in Joshua 5:15. Suddenly, Joshua was approached by "the captain of the Lord's host" (whoever that might have been) and told: "Remove your sandals from your feet, for the place where you stand is holy." Both times, the holiness is derived from the presence of the Lord and it does not outlast the experience. The parallel event in Joshua was key to his authorization and authentication as Moses' successor.
Joshua led the people into the land of promise; Moses stayed behind. Entering the Promised Land had more to do with the fulfillment of God's promise to Abraham than to the issue of holiness. But there is no reason to believe that Moses was being "punished" by not having this experience. His commission was to bring the people out of Israel and he surely fulfilled that.
Having said that, however, the insight behind the question is inspiring. It hints again at the completeness of Moses' experience, and his unique relation to God. He was spared the challenges of settling in the land of promise thereby making it possible for him to spend his time with God. He needed no other reward.