When you say that Israel lived in booths for the entire forty years in the desert or in the same year the set forth out of the land of Egypt did Israel first live in booths the same day they set foot out of the land of Egypt or were there more than 40 days and 40 nights after they set foot out of the land of Egypt when the Lord first had the children of Israel first live in booths?

They lived in Sukkot for 40 years in the desert. Sukkot, are temporary living quarters, and in memory and thanks for God protecting us under such difficult and temporary conditions, Jews dwell (including eating and sleeping) outside in temporarydwellings for 7 days a year during the holiday of Sukkot (Tabernacles). There are many technical halachic requrements which must be observed today to fulfill the mitzva of Sukkot, but that doesn't mean that Israel had to observe all those laws from the very first day and for all 40 years, for they very well may have sometimes slept under the stars or in simple tents during those 40 years.The main point is that they lived in temporary dwellings.