The first thing that comes to mind on that verse from a Jewish reading is the outright connection to Jewish language about the Messianic Age.
As in the many references to the prosperity to be enjoyed under the Messiah (for example Micah 4:4), Jesus links a fig tree to the approach of "summer," which by no coincidence is being used as an example of the approach of his promised Parousia. Summer is when the fig is in season, and having one's personal source of in-season figs is the symbol of the Jewish concept of Messianic rule.
Recall that God during the Exodus promised the Israelites that they would be brought to a land "flowing with milk and honey"? The "honey" is not what most Westerners or Gentiles think it is. The actual Hebrew word refers to a syrupy jelly that was used as the main sweetener as sugar and syrup is used today. While the same word was used to describe the honey made by bees, it's main meaning is this sweet jelly. You can make it from fruits like grapes, but especially for the Jews in the land of Israel, this "honey" was made from figs.
From the very beginning, life in the Promised Land was to be idyllic, and the honey of figs was symbolic of the prosperity God wanted for his people. As Micah 4:4 states, in the Messianic Age each Jew shall "sit under their own vines" from which they make wine "and under their own fig tree" from which this main symbol of "honey" was produced.
While Jehovah's Witnesses are apt to say that Jesus is telling people to interpret world events to know when the end is near (which has caused them much egg on the face for constantly being wrong), Jesus might be saying something far more simpler. It seems like he his saying that once his followers find themselves in the thick of the time of the end, they should be at ease for this is a sign that "summer is near." The "fig tree" is in bloom, symbolically speaking, when it becomes undeniable that the world has reached its end. In other words Jesus is saying to be hopeful.
Unfortunately, the Witnesses have taken a symbolism of hope in the midst of crumbling world events to be a measure of time. Because verse 34 about the "generation" follows immediately after, they assume that Jesus is saying that when you see all the signs of the end, it is like seeing that a fig tree has all its leaves. That doesn't seem likely because Jesus spoke and taught like a Jew. Using a fig tree is not a coincidence. A Jewish sage would never do that and switch a symbol of Messianic prosperity and suddenly make it a symbol of a time indicator measuring how close we are to the end.
While I can't say for sure if there is meant to be a way to understand "generation" as a literal measurement of time (there might be), there is likely no literal connection between the fig tree and the time factor. It is just the Jewish way of saying what Luke (in his gospel for Gentiles) adds: "When you see all these things taking place, you know that the kingdom of God is near." ( Luke 21:31) The direct reference to the kingdom is not there in Matthew. Why not? Because the fig tree is used, and Matthew was written mainly for Jewish Christians who understand what the symbol means.