What is the meaning of "Ger ve'Toshav"?
Rashi (citing Targum Onkelos) and Ramban: It means 'a Nochri who sojourns with you'. 1
Targum Onkelos and Targum Yonasan: It means a Nochri and a Toshav. 2
Sifra: "Ger" refers to a Ger Tzedek, and "Toshav", to a Ger Toshav. 3
Da'as Zekenim: "Ger" refers to [exile under] Malchus Madai; "Toshav", to Malchus Yavan, and "Mishpachas Ger", to Malchus Romi, which will be uprooted.
Rashi's text in Targum Onkelos reads "Areil Tosav". See answer #2.
Whereas "Ger Toshav" later in the Pasuk they tranlate as 'Ve'yizdaban le'Areil Tosav' (one person). "Ger" cannot refer to a Ger Tzedek, as it did in Pasuk 35 - Refer to 25:35:3:1 - since the Pesukim that follow indicate that the Torah is speaking about a Nochri who worships idols (Nachlas Ya'akov).
Why does the Torah insert the words "Yad Ger ve'Toshav Imach" and "u'Mach Achicha Imo"?
Rashi: To teach us that the Nochri became rich because he cleaved to us and our brother became poor because he cleaved to the Nochri and learned from his ways. 1
See also Oznayim la'Torah.
What are the connotations of "O le'Eiker Mishpachas Ger"?
Rashi: "Mishpachas Ger" refers to the Nochri ? the family of the Ger and "Eiker" 1 to the Avodah-Zarah, to which he will ultimately be sold, not to worship it, 2 but to chop wood and draw water in its service.
Ramban (based on Targum Onkelos): Refer to 25:47:1:2*. "Eiker" refers to the Nochri 3 - the family of the Ger Toshav, whose living among us caused our brother to be sold to them.
Rashbam: "Eiker" refers to a Nochri who has moved to a country that is far away from yours. 4
Moshav Zekenim and Ba'al ha'Turim ha'Aruch (based on Targum Onkelos): The Ger Toshav who became rooted among Yisrael caused your brother to be sold to his family.
Ramban and Moshav Zekenim: So-called because one must root it out ('La'akor Acharehah').
Since that lies within his Bechirah ? to worship it or not.
Ramban: So-called because he is from the same root as the Ger Toshav - as in Daniel, 4:12.
And "Eiker" is from the word 'Ne'ekar' (op-rooted).
Why does the Torah permit a Yisrael to sell himself to a Nochri?
Refer to 25:39:2.1:1.