1) Ch. 37, v. 34: "Va'yisa'beil al b'no yomim rabim" And he mourned for his son many years Rashi explains that Yaakov mourned for the loss of Yoseif for 22 years, the same amount of time that he was away from his parents (save time spent in Yeshivas Eiver). Yitzchok told Yaakov to leave home to pursue finding a wife so why is this time counted against him?
2) Ch. 37, v. 35: "Va'yimo'ein l'hisnacheim" And he refused to console himself Rashi explains that although Hashem set into a person's psyche to forget the sorrow of the death of a loved one after the passing of a year (gemara P'sochim 54b), there is no consolation when the assumed deceased is actually alive (maseches Sofrim ch. #21). If so, why didn't Yaakov himself realize that Yoseif must still be alive?
3) Ch. 38, v. 14: "Va'teishev b'fesach einayim" And she sat at a road junction This is Rashi's interpretation. The reason that a road junction is called "pesach einayim" is because one has to open his eyes, i.e. pay special attention at a junction, so that he continues his trip on the proper path (Rabbeinu Menachem and Pirush al Targum Yonoson ben Uziel). If this is so, why in verse 21 do we only have "vo'einayim al ha'derech," without "pesach"?
4) Ch. 38, v. 25: "V'hee sholchoh el chomihoh" And she sent to her father-in-law Rashi (gemara Brochos 43b) says that Tomor did not simply say that Yehudoh impregnated her. Rather she only sent the payment, saying, "The man to whom these items belong is responsible for my pregnancy. If he admits it fine, and if not, let them burn me rather than my embarrassing him." From this we derive that it is preferable for a person to throw himself into a fiery cauldron rather than embarrassing his fellow man.
The Baal Haturim and Rabbi Yehudoh Chosid say that Yehudoh's words of the previous verse, "Hotziuhoh v'siso'reif," do not mean that she was to be burned to death, but rather, that a mark be made on her face with a burning brand, as a constant sign to her sin. If so, what is the proof that it is preferable to be burned to death, as that wasn't going to be her punishment? As well, how do we derive that it is preferable to "throw oneself" as she was not about to do this to herself, but rather, it would be done by others?
5) Ch. 39, v. 9: "V'chotosi lEilokim" And I will have sinned against Elokim Yoseif did not justify his refusal on moral grounds, i.e. adultery is a morally wrong act, or that he might be caught. He simply said that this was against Hashem's wishes. Why did he not say the former?