Who was Chovav ben Re'u'el?
Why does the Torah insert the words "Oso Etein lachem"?
Sifri: To extrapolate "Lachem", 've'Ein le'Geirim Cheilek bo' - Geirim do not inherit a portion in Eretz Yisrael. 1
Torah Temimah, citing the Sifri explains that, based on a Pasuk in Yechezkel, 47:23 - they can inherit a place to be buried.
Why did Moshe say to Yisro "L'cha Itanu" and not 'N'sa Itanu'?
Oznayim la'Torah: Because the term 'N'sa' in this context refers to the order in which the tribes traveled, 1 and Yisro who was a Ger, was not permitted to travel together with any of the tribes.
What 'good' was Moshe referring to when he said to Yisro "L'cha Itanu Veheitavnu lach"?
Oznayim la'Torah: He was promising him a portion in Eretz Yisrael - Doshnah shel Yericho. 1
Yerushalmi Bikurim, 1:4: He was referring to the merit of Yisro's descendents to bring Bikurim from the fruit of their fields and to recite the Parshah over it. 2
What was Moshe referring to when he told Yisro "Ki Hashem Diber Tov al Yisrael"?
Ramban: He promised him a portion in the spoil that they would capture from the Cana'anim - silver, gold, clothes, sheep and cattle. At least, that is what Yisro understood.
Targum Yonasan: He was referring to the good that Hashem promised He would bestow upon Geirim. 1
See Na'ar Yonasan.
It would be a long time before Yisrael entered Eretz Yisrael. What did Moshe mean when he told Yisro "Nos'im Anachnu el ha'Makom ... "?
Rashi: They were actually leaving Har Sinai with the intention of arrriving in Eretz Cana'an in three days time, 1 only they sinned by the 'Mis'on'nim' (the complainers [following which one thing led to another ... ]).
See Sifsei Chachamim.
QUESTIONS ON RASHI
Rashi writes that Moshe included himself ("We are traveling? to Eretz Cana'an) because it was not yet decreed that he will enter and he thought that he would enter. - whereas In Sh'mos (4:13), he wrote that Moshe knew that he would not take B'nei Yisrael into the land?
Refer to Sh'mos 4:13:151:1-3.
Oznayim la'Torah: To be sure he knew that he would not enter Eretz Cana'an, only he declined to mention it here 1 for any one of three reasons 1. In order not to shock Yisrael; 2. So that Yisro should not say that if Moshe was not destined to enter Eretz Cana'an, what were all his promises worth? 3. He still hoped that Hakadosh-Baruch-Hu would cancel the decree 2 and allow him to enter after all.
Rashi writes that they delayed in the Midbar forty years due to the sin of the complainers. The Mechilta (Pesichah to Beshalach) says that Hashem delayed them so they could learn Torah when their food and water is supplied, or to enable that the Cana'anim to fix what they had destroyed, so that Yisrael would inherit a land filled with good?
Riva (Sh'mos 16:35): Rashi does not mean that the forty years were decreed due to the complainers, but that, through the sin of the complainers, it transpired that they did not enter Eretz Yisrael.
It is impossible to understand the Mechilta at surface value - seeing as the Torah in Sh'lach-L'cha, 14:21-24, specificaly ascribes the delay to the soin of the spies (which was an indirect result of the sin of the Mis'on'nim). We must therefore say that Hashem had both reasons in mind - one to punish the older generation, the other, to prepare the land for the new generation