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Yaakov gives Yosef what many commentators assume is the actual city of Shechem as an additional inheritance (see Genesis 48:22, especially according to Rashi's interpretation). Why did Yaakov choose to give that specific city to Yosef?
I realize he says that he conquered it himself, but I don't know if that is a reason for giving it, especially in light of the commentaries who say that Yaakov didn't actually conquer it himself (Shimon and Levi did).
Ramban on that verse answers that the city of Shechem was the only portion of the Land that Yaakov could give to Yosef, as it was the only one that was under his control. Here's his conclusion, though it's worthwhile to read the entire piece.
והנה אמר לו עשיתי עמך כל הטובה שיכלתי לעשות לך לעת שהייתי יכול לעשותה כי אין ברשות יעקב בארץ רק שכם אחד שאין בידו לגזול מאחד מבניו את נחלתו רק הבכורה היתה לו לתת אותה לטוב בעיניו והנה נתן אותה אליו
Thus, Yaakov said to him Yosef: "I have done for you all the good that I was able to do at this time," because the only portion (שכם) of the Land that Yaakov had control over was the portion of the firstborn; he was unable to give Yosef any other portion, because he couldn't "steal" from his other sons' inheritances. The only thing he could give Yosef was the firstborn portion, which was his. Therefore, this is the part that he gave to Yosef.
(translation mine, loosely based on Artscroll's)
Perhaps the message is the following... Shechem was the city where Yosef was abducted and sold and had become the symbol of sinat chinam. The gift of Shechem from Yakov may be a symbol of Yakov's gratitude to Yosef for forgiving his brothers thereby restoring the hope that the misery of Shechem can be transformed into a future of hope and unity
Nature their Nurture (p. 139) shares a beautiful insight about Shechem:
Shechem is the place where people throughout our history have been drawn to regain their power in life. How exactly did they come away from the encounter with Shechem with more energy? It somehow focused them on their core greatness, their unique portion. The Shem MiShmuel (Vayishlach 5762) calls this hinas'us, the elevation of the self. Upon entering Eretz Yisrael, Avrhaham went to Shechem to draw strength. Yaakov went to Shechem after years of personal exile in order to get his power back. And Yehoshua takes Klal Yisrael there as soon as possible to seal the covenant and returns there before his death to fortify it. They did this knowing that in Shechem lies a great danger. The Torah shows us up cloe the damagaing, intoxicated delusions of Shechem bas Chamor. A place that helps people focus on their perosnal greatneess carries the risk of causing them to think of thesmevles as more than what they really are, and conseqeuntly to grow out of touch with the people around them. This is what happened to Yosef's brothers when they gathered in Shechem to garner strength after feeling deflated in the wake of Yosef's dreams, but it was also there that they turned around and ended up condemning him to death. This is why Yeravam ben Nevat established his breakaway monarchy there as well, with the belief that the Northern Kingdom of Israel could exist independent from Yehudah, Binyamin, and Yerushalayim.
Perhaps Yaakov Avinu realized Yosef HaTzaddik exhibited the necessary inner strength to harness the power of the esteem-boost provided by Shechem, and would best use the potentially dangerous gift. Yosef showed profound self-restraint in the immorality of Mitzrayim regardless of being in the lowliest or highest of positions.
A second answer I think I heard from Rabbi Frand is that Yaakov saw Yosef had the incredible bitachon/power to turn a painfully tragic situation into one of tremendous success - as evidenced through everything Yosef went through as a slave until becoming a leader of Mitzrayim while still holding steadfast to Hashem. Therefore, Yaakov wanted to give the tragedy-filled city of Shechem to the one person who personified transforming sadness into happiness.
See here . While this iste seems to focus on Kabbalist views, this specific article, I think, mentions so "practical" (non Kabbalistic) reasons. Excerpts:
Rashi's comments point to the many distinct facets of the city Shechem, and the rich meaning of the place. First, Rashi mentions Shechem's role as a place of burial, given as a reward for performing this great mitzvah. Joseph performing this mitzvah leads to an incredible "chain of mitzvahs," performed by ever higher entities. The mitzvah of burying Jacob is charged to Joseph, whose burial is charged to Moses, whose burial, in turn, is performed by Hashem himself. (See Talmud Sotah) After Moshe passes, it is Joshua, a descendant of Joseph from the Tribe of Ephraim, who is charged with actually burying Joseph inside the Land of Israel. Interestingly, the passage quoted by Rashi is actually juxtaposed with Joshua's own passing. Even more fascinating is the fact that both Joshua and Joseph were 111 years old when they died. One could speculate about whether Joshua and Joseph were not in fact one and the same.
Rashi then explains how Shechem is associated with the extra portion of the firstborn. Shechem has many other associations with being the "first:" Shechem is the first place visited by Abraham, Jacob, as well as Joshua when entering the Land of Israel. Even in modern times, the first settlement established in Judea and Samaria after the Six Day War was Elon Moreh, which is another biblical name for the city Shechem. Shechem is the gateway to the Land of Israel.
Related to the above, Rashi then notes that Shechem was taken from Eisav, who behaved like an Amorite and lied to his father. Jacob is characterized by the fact that all of his children remained true to their Judaism and Jewish identity (Mitatoh Shleimah - "his bed was complete"). Furthermore, Jacob is associated, first and foremost, with the truth ("Titen Emeth L'Yaakov," "Give truth to Jacob"). The Torah also states that Shechem was acquired monetarily by Jacob (similar to how Jacob acquired the birthright), and that it is one of the places that Gentiles are unable to even claim that they were stolen by the Jews. (Genesis 33:18-19; Midrash Rabbah)
The article cites other connections / reasons as well.
