Two parshas ago many wondered why Yitzchak would have tried to give his blessing to Esav. The answer to that can be seen by working backward from the blessing.
Yitzchak blesses the son he thought was Esav by saying, "The smell of my son is as the smell of a field which the LORD hath blessed." The blessing that he goes on to give him is the blessing of the field.
"God give thee of the dew of heaven, and of the fat places of the earth, and plenty of corn and wine. Let peoples serve thee, and nations bow down to thee. Be lord over thy brethren, and let thy mother's sons bow down to thee."
To secure this blessing, Yitzchak had sent out Esav to take his weapons and hunt him down a meal. Esav was the hunter, the one who went out and caught game, while Yaakov dwelt in tents, watching over the flock as a shepherd. While Esav goes to hunt meat, Yaakov slaughters tame animals for the meal.
Yaakov is the shepherd. Esav is the hunter. But Yitzchak chose to favor the son who was the hunter. And this makes a certain amount of sense when you consider that the blessings of Avraham that he passed on was to dominate the land. Who was more likely to dominate the land, a mild-mannered shepherd who dwelt in tents or a bold aggressive hunter?
Yitzchak, as a shepherd, had spent this time being hounded by the Philistines, driven from his father's wells and grazing lands, with no recourse. The son he favored was the one he thought would be able to stand up to the Philistines and fight for what was his.
Now when Yaakov and Esav meet again in Parshas Vayislach, Esav has become the hunter and warrior with an army at his back, while Yaakov is a shepherd, with a camp of people and animals. Both sons have become more of what they were all along. Esav has 400 warriors at his call and Yaakov has an army of sheep and other livestock. Esav dwells on his own mountain while his brother still wanders, pitching his tent, and trying to avoid persecution.
Yaakov pays tribute to his brother, in the form that a shepherd values, in animals, Esav does not appear to appreciate the tribute, but does approve of his brother's submission, and goes on his way. Esav offers to escort Yaakov, but Yaakov tells him that the flocks cannot keep up such a pace. Esav returns to his mountain and Yaakov builds barns for the flocks, and names the place after the barns, Sukkos.
Why name a place after the barns? Because they showed the contrast between the two brothers. Between the hunter and the shepherd. Esav was more vital, and in the short term, the dominant one. The genealogy at the end of Parshas Vayislach lays out how many kings and princes Esav had. But in the long term, the house of Esav went into a decline, while the house of Yaakov continued to grow.
By the end of the parsha, Esav is formed to move on, because Yaakov's flocks have grown so much that the land cannot support them both. The shepherd had already won.
Yitzchak was correct in assuming that one day his descendants would have to fulfill the blessings by conquering the land. And it's easy to see why he would have chosen Esav as the favored son, the one strong enough to do it. But conquering the land, is not the same thing as holding it.
Esav was more aggressive than his brother, not necessarily stronger. Yaakov was a shepherd and capable of building for the long term. Esav had power, but not endurance. That was how he came to give up his birthright for a mess of pottage. Esav could not have worked for twenty years for Lavan the way Yaakov did.
While Yaakov exerted himself to build a long term future, sacrificing the present for the future, Esav lived entirely in the present, satisfying himself with short term accomplishments of the moment. As a hunter, he lived for the next kill, while Yaakov built armies of flocks. That was one reason why Yaakov represented the destiny of the descendants of the patriarchs, while Esav did not. Instead Esav was a dead end.