Moses continues addressing Israel in the second singular, except for you may multiply greatly, which is plural.
Hear therefore, O Israel: Hear is an attention-getter: “Listen to me, people of Israel!”; “Pay attention, Israelites!” This vocative addresses all the people as one individual. “Listen to them” (Good News Translation) departs needlessly from the meaning of the Hebrew text.
Be careful to do them: this is a way of saying “Do your best to obey them” (see 5.1).
That it may go well with you: obedience will bring blessings of prosperity and peace (see the same language in 5.29).
That you may multiply greatly: this means to have many descendants. Both Good News Translation “a mighty nation” and Contemporary English Version “a successful and powerful nation” emphasize the consequence of being a nation with a large population; it is better to stay close to the immediate meaning of the Hebrew text (see 1.10).
The God of your fathers: fathers refers to their ancestors, especially Abraham, Isaac, and Jacob (see 1.8 and 6.10).
A land flowing with milk and honey: this is traditional language (see Exo 3.8), meaning “a rich and fertile land” (11.9; 26.9, 15; 27.3; 31.20). Many modern translations still keep the biblical figure (New Revised Standard Version, Revised English Bible). The meaning is that the land is a good one for large herds and flocks (milk), and for crops and fruit trees (honey is probably the thick syrup produced from dates, not wild honey made by bees). In some languages this phrase has been deeply established in the Christian vocabulary and may need to be retained, but in many other languages a literal translation will be meaningless. In such a case “rich and fertile land” (Good News Translation) will be a suitable alternative model. We may also say something like “a land full of cattle and many crops (or, much fruit).”
Quoted with permission from Bratcher, Robert G. and Hatton, Howard A. A Handbook on Deuteronomy. (UBS Helps for Translators). New York: UBS, 2000. For this and other handbooks for translators see here .