After reading the chapter in Numbers, what I would say is what leads to the wilderness generation’s condemnation is the way in which the people no longer trust God as much and start complaining a lot about the food and their lifestyle as they are reaching the promised land. Also, the way in which the spies that were sent to the land discourage the people and tell them that they have no chance for beating the current inhabitants of the land and make them distrust in God makes God very angry at them. The people disobey God and try to take things for themselves instead of letting God give them what he promised. This goes back to the difference between giving and taking that was the origin of the discommunion between God and people.
I think that they chose to end the Pentateuch right after Moses dies in order to signal a shift. It is described that no other prophet is as good as Moses because of how he knew the Lord face to face, and thus finishing this section of the Bible with his death emphasises largely on how there is now a change in the prophets. Moreover, I think that it signals a shift between the Israelites being punished and suffering, to how now they are able to enter into the promised land and begin to have more conquests.
The chapters from Joshua and Judges show how even though the Isreaelites are able to conquer the land and be successful in doing so, they still struggle with remaining loyal and worshiping only God. They fall easily to the worship of other idols, which angers God and makes him punish the people of Israel. It shows again a cycle in which the people of Israel grow restless and start to walk away from God until they are faced with some type of punishment that brings them closer to Him again. The closing passage of Deuteronomy guides our readings of Joshua given how it shows the way in which it claims that no prophet will be like Moses was. It talks about how the generation of Moses was the one with the closest attachment to God and how from then on the Israelites will continue to have a hard time following God’s ideals and laws.
Alegria Ubidia 
Your reasoning for choosing to end the 5 premier books of The Bible with Moses’ death was not only reasonable but quite sound, and supplemented my idea that this is a large shift in the story. Still, you recognize that Moses’ importance remains.
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