What are the ramifications of "Vekidashtem"?
Rashi: When the year begins, 1 Beis-Din announce 'Mekudeshes ha'Shanah!'
Sifsei Chachamim: And not on Yom Kipur.
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 Beno Shel R. Yochanan ben Berokah): On Rosh Hashanah the Avadim ceased working, and their erstwhile masters arranged parties for them, and on Yom Kipur, they released them.
What are the ramifications of "u'Kerasem Dror"?
Rashi: 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: Dror is an expression of clean (without obligation to serve a master), i.e. a free man.
What are the implications of the word "le'Chol Yoshvehah"
Rashi (in Megilah, 14b): It implies that Yovel only applies when all its inhabitants 1 are in Eretz Yisrael, but not when some of them are in Galus.
With reference to all 12 tribes (See Torah Temimah).
What are the connotations of the words "Yovel Hi"?
Ramban, Moshav Zekenim: It is based on freedom; everyone is free to go and live wherever he wants. It refers to coming; everyone comes back to his inheritance and hjs family.
What are the implications of "v'Shavtem Ish el Achuzaso"?
Rashi and Rashbam: It implies that his fields are returned to him. 1
Sifsei Chachamim: Because, when a man's field is returned to him, it is as if he returns to his field.
What does the phrase "v'Ish El Mishpachto Tashuvu" teach us?
Rashi: It teaches us that a 'Nirtza' (an Eved Ivri who had his ear pierced) returns to his family in the Yovel.
Rashbam: It teaches us that all Avadim Ivrim go free in the Yovel, without having to compensate their masters.
Moshav Zekenim (from Kidushin 21b): It teaches that a Kohen cannot become a Nirtza 1 , because he becomes a Ba'al Mum; he does not return to the Chazakah of his family. Some Seforim learn this from "v'Shav El Mishpachto." This is a mistake; that verse does not discuss a Nirtza!
QUESTIONS ON RASHI
Rashi writes that "u'Kerasem Dror" is even for a Nirtza. He also says that "v'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; "v'Ish El Mishpachto" teaches this.
Sifsei Chachamim #1: The primary source is from "v'Ish El Mishpachto." Based on this, we know that "u'Kerasem Dror" is even for a Nirtza.
Sifsei Chachamim #2: One might have thought that "u'Kerasem Dror" is only for a Nirtza who [initially] sold himself. "V'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 Shemos 21:6:152:1