What is the meaning of "li'Schok Osim Lechem [v'Yayin Yesamach Chayim]"?
Rav Sadya Gaon: They make meals for Simchah.
Rashi: For the pleasure and amusement of Chasanim and kings, they make a meal. A big meal is called Lechem - "Belshatzar Malka Avad Lechem Rav" (Daniel 5:1).
Ibn Ezra: Every Simchah and laughter in the world, it is primarily with bread and wine, which gladdens man's life. Perhaps "Chayim" is an adjective; wine gladdens the living.
Rashbam: Those who jest, they have bread.
Ri Kara: They make a meal for the need of jesting and Simchah. A meal is called Lechem - "Madu'a Lo Va Ven Yishai Gam Temol Gam ha'Yom El ha'Lechem" (Shmuel I, 20:27).
Metzudas David: Only for Simchah, people make a big meal; it is not common to do so.
Metzudas Tziyon: Sechok is joy.
Why does it say "v'Yayin Yesamach Chayim"?
Rashi: This is the drink at the meal [that rejoices people].
Rid: One who drinks wine, it gladdens him.
Seforno: This is when the king and the officers turn to drinking.
Metzudas David: This is for healthy 1 people. For people of weak nature, wine brings sadness.
Metzudas Tziyon: "Chayim" is healthy, like "Ad Chayosam" (Yehoshua 5:8) - until they healed and became healthy.
What is the meaning of "veha'Kesef Ya'aneh Es ha'Kol"?
Rav Sadya Gaon: Money brings (enables one to get) everything. Ibn Ezra - Ya'aneh is to make available, when its owner desires. Perhaps Ya'aneh is from the root Es; the middle letter of the root (Nun) is omitted, like I explained above (9:11).
Rashi: If there is no money, there is no meal. Therefore, one should not be lazy from working, so he will have what to spend. Rashbam - Ya'aneh is an expression of doing.
Ri Kara: All need an Ashir.
Seforno: Money of bribes and coveting money lowers everything - the country and those who lead it, when Tzedakah and Mishpat depart from it.
Metzudas David: Money fulfills everyone's request 1 , for all need it - whether for Simchah or another matter, whether healthy or weak. This refers to the previous verse. All need money; due to laziness, he lacks money!
Metzudas Tziyon: Ya'aneh is an expression of answering, like "E'eneh Es ha'Shamayim" (Hoshe'a 2:23).