1)

Why does it say "ba'Shir Lo Yishtu Yayin"?

1.

Radak: The way of revelers is to drink amidst singing. They will sigh; there is no song in their mouths.

2.

Malbim: Not only did songs with musical instruments cease - they will not even sing vocally while drinking wine.

2)

Why does it say "Yemar Shechar l'Shosav"?

1.

Radak: The little strong drink that they will drink will be bitter in their mouths, amidst many Tzaros.

2.

Malbim: Strong drink converted to be bitter; it is given "l'Marei Nafesh" (Mishlei 31:6).

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