Listening to Mordechai ben David's song "את אחי אנכי מבקש" I was struck with the following thought, which is an extension of the previous discussion of Yosef and Shechem.
Yosef asked Gavriel where his brothers had gone, and where they were shepherding. First, it is significant that he was speaking to Gavriel, because we find that the side of Gevurah (the left side, represented by Gavriel) comes into play immediately before redemption. Thus, this question was clearly marking a step toward redemption, and specifically in Yosef's role as Moshiach ben Yosef. If not for Gavriel, Yosef would not have found his brothers, and the process would not have begun.
Gavriel guides Yosef at Shechem, sending him to Dotan where he finds them, and they plot to kill him. Thus, besides for Shechem representing the place where Yaakov sacrificed to keep Yosef as Moshiach ben Yosef, it would also be the place where Yosef would begin his function of Moshiach ben Yosef - the tzaddik who would suffer in order to create a balance. If you listen to the fifth Moshiach podcast, you will see how Yosef fits this concept.
Yosef ends up suffering significantly more, but also ends up with a greater share in Klal Yisrael - two tribes. His greater challenge means that he will end up with more, but also means that he must go through more to attain that greater level.
It is interesting that both Yosef and Esav exhibited characteristics that showed they were naturally more involved in the physical world. Esav would end up falling into the trap and losing his extra portion and then even any portion in Klal Yisrael. Yosef would utilize his extra physicality (e.g. his good looks), and raise it up by withstanding his travails so that he would indeed earn his double portion in the Jewish people, and seemingly in the World to Come as well.
One last thing, is that Rav Kessin says that Moshiach ben Yosef goes through stages, progressing from the letter סמך to the letter שין (sin) to the letter שין (shin). The סמך represents the first level סכל - literally, the fool. At this stage, Moshiach ben Yosef is not aware of his mission, nor of how to accomplish it. The passuk in Yeshaya 53, in reference to Moshiach ben Yosef, says "הנה ישכיל עבדי" - my servant shall become wise. This is the middle stage where Moshiach progresses from the level of סכל to שכל - from fool to wisdom. This is the level of the letter שין (sin). Here he understands how to rectify his personal trials. Finally, he reaches the level of the שין (shin). Here he moves from the left (represented by the שין with the dot on the left) to the right (represented by the שין with the dot on the right), and moves toward teaching Klal Yisrael how to achieve their rectification as well.
I believe that this whole concept is actually hinted to in the name of the city Shechem. If you take the gematria of the word שכם, you get 360, or שס. Thus, it represents a place where there is a progression involving these letters, סמך and שין, leading to the rectification necessary for the advent of Moshiach ben Yosef.