What is the connection between this Pasuk and the previous one?
Rashi: 'If you will do your job, then I will do Mine!' 1
Rashbam: 'If you serve Hashem with love, Hashem will provide for you in a way that you will eat and be satisfied without any effort'.
Seforno: 'If you serve Hashem with love, Hashem will sustain you without effort on your part, in order that you continue to serve Him. 2
What are the connotations of the word "b'Ito"?
Rashi #1: At night-time, 1 when nobody is disturbed by the rain.
Rashi: On Friday night, 2 when everybody is at home.
What is the difference between "Yoreh" and "Malkosh"?
Rashi and Targum Yonasan: "Yoreh" is the early rain 1 - following the planting (in Marcheshvan - Targum Yonasan), and "Malkosh", the latter rain, 2 just before the harvest (in Nisan - Targum Yonasan).
Lev Eliyahu (Shemos p.91 citing the Vilna Gaon): Yoreh hints to prophecy, and Malkosh to Ru'ach ha'Kodesh. Degancha v'Siroshcha v'Yitzharecha are Chachmah, Binah and Da'as. V'Achalta v'Savata are Halachos and Agados.
Rashi: So-called because it satiates (Marveh) the ground and the seeds. Hadar Zekenim
What are the implications of "V'asafta Deganecha"?
Rashi: It implies that you will gather your grain, and not your enemies. 1
Hadar Zekenim #1, Da'as Zekenim #1: After this, rain will not come, for rain at the harvest time is a curse