Did Israel enter the Promised Land under the same favorable circumstances as they could have had 40 years earlier?
No. Israel entered the Promised Land from the east side of the Jordan at flood time, after Moses had died and Joshua assumed leadership. It remained the land of promise, but not under the circumstances they could have had forty years earlier.
Les explains that Israel had been brought all the way around through Moab and was encamped on the east side of Jordan at flood time. Moses had gone up into Mount Nebo and died, and Joshua picked up the reins of leadership as the nation prepared to go in and occupy the promised land. It was still more or less the land of promise, but certainly not under the circumstances they could have had forty years earlier. Les also notes that Deuteronomy ends with Moses’ death, just as Genesis ended with Joseph’s death, and that God buries His servants but never His program, so the passing of great men did not interrupt the fulfilling of all God’s purposes.
More Questions
Were the circumstances of the promised land the same when Israel entered it after 40 years as they would have been earlier?
When Israel finally entered the promised land, it was still the land of promise, but their circumstances were not as favorable as they could have had 40 years earlier.