Dwelling in sukkot in the wilderness epitomizes a life of uncertainty as to what will happen tomorrow.
That uncertainty precludes building permanent structures; it allows only for temporary booths.
When the people of Israel entered the Land and settled in it, their lives changed dramatically from an unattached, up-in-the-air existence to a life of permanence and relative security.
Such a life affords the possibility of planning for the future, establishing a permanent place of residence, and building permanent living quarters.
The nation’s stable life in the Land of Israel was the people’s dream when they were wayfarers in the wilderness.
The Promised Land, “a good and spacious land,” “where you will lack nothing,” was their aspiration and goal ever since the exodus from Egypt.
After this goal was realized, however, after life became stable, and permanent residence was achieved, the Torah’s command was to recall the former period in the wilderness, the wandering and impermanence.
–Rabbi Adin Steinsaltz