What are the ramifications of "Vekidashtem es Sh'nas ha'Chamishim"?
Rashi: When the year begins, 1 Beis-Din announce 'Mekudeshes ha'Shanah' at the beginning of the year!
How do we reconcile this Pasuk, which implies that Yovel commences on Yom Kipur, with the previous Pasuk, which implies that it commences on Rosh Hashanah?
Rosh Hashanah, 8b (citing R. Yishmael B'no Shel R. Yochanan ben Berokah): On Rosh Hashanah the Avadim ceased working, and their erstwhile masters arrange parties for them, and on Yom Kipur, they release them.
What is the meaning of "u'Kerasem Dror"?
Rashi, Targum Onkelos and Targum Yonasan: It is an announcement of freedom 1 for all Avadim Ivrim, both those who have not yet served six years and those who have had their ears pierced.
Ramban (according to Kabalah): It is an expression of 'Dor' (generation). 2 And by the same token - 'it will return to his roots (with reference to "Yovel" in Pasuk 11).
Rosh: D'ror is an expression of clean (without obligation to serve a master) - a free man.
Rosh Hashanah, 9b: "D'ror" means freedom
What are the implications of the word "le'Chol Yoshvehah"
Rashi (in Megilah, 14b) and Rashbam: It implies that Yovel only applies when all its inhabitants are in Eretz Yisrael, but not as long as some of them are still in Galus. 1
Erchin, 32b: When Reuven, Gad and half of Menasheh went into Galus, 2 the Yovel ceased to apply, and even if all the tribes are there, but not in their correct locations - mixed-up, Binyamin together with Yehudah or vice-versa. 3
What are the connotations of the words "Yovel Hi"?
See Sifsei Chachamim.
See also Ibn Ezra in Sh'mos 19:13.
See Torah Temimah, note 56.
Why does the Torah insert the (otherwise superfluous words "Yovel Hi Tih'yeh lachem"?
Ramban #1 (according to Rashi): It should be for you all a reminder - to the Avadim Ivrim to go free and the to the purchasers to return the property to its original owners.
Seforno: To teach us that the purchasers too should be happy to free the Avaidin Ivrim and to return the land to the original owner. 1
What are the implications of "ve'Shavtem Ish el Achuzaso"?
Rashi and Rashbam: It implies that the original owner's fields are returned to him. 1
Sifsei Chachamim: Because, when a man's fields are returned to him, it is as if he returns to them.
What is the phrase "ve'Ish el Mishpachto Tashuvu" coming to teach us?
Rashi: It teaches us that a 'Nirtza' (an Eved Ivri who had his ear pierced) returns to his family in the Yovel. 1
Rashbam: It teaches us that all Avadim Ivrim go free in the Yovel, without having to compensate their masters.
Moshav Zekenim (citing Kidushin 21b): It teaches us that a Kohen cannot become a Nirtza 2 , because he becomes a Ba'al Mum and cannot therefore return to the Chazakah of his family.
Targum Yonasan: It teaches us that Avadim Ivrim revert to their previous Yichus (position of importance).
The Gemara in Kidushin, 15a learns this from the word "Ish"
Why does the Torah insert the (otherwise superfluous) word "Tashuvu"?
Sifra: To teach us that also a girl who has been sold (as an Amah Ivriyah) goes free in the Yovel.
QUESTIONS ON RASHI
Rashi writes that "u'Kerasem Dror" is even for a Nirtza. He also says that "ve'Ish el Mishpachto Tashuvu" teaches this?
Divrei David: Had it said only "u'Kerasem Dror", one might have thought that he is free, but he does not return to the Chazakah of his family; "ve'Ish el Mishpachto" teaches this.
Sifsei Chachamim #1: The primary source is from "ve'Ish el Mishpachto." Based on this, we know that "u'Kerasem D'ror" is even for a Nirtza.
Sifsei Chachamim #2: One might have thought that "u'Kerasem D'ror" is only for a Nirtza who [initially] sold himself. "ve'Ish el Mishpachto Tashuvu" includes even one who was sold via Beis Din.
Rashi writes that Yovel has its own name, based on after the ram's horn. Any Shofar is Kosher for Yovel. It need not be from a ram!
Refer to 25:10:5:2 & 3.
Rashi writes that Yovel frees all Avadim Ivrim, even a Nirtza. What is the source to free one who did two Aveiros, i.e. theft, and choosing to become Nirtza?
Refer to Sh'mos 21:6:152:1