What is Shlomo's vineyard?
Rashi: It is Keneses Yisrael - "Ki Kerem Hashem Tzevakos Beis Yisrael" (Yeshayah 5:7). Seforno - Melech ha'Mashi'ach says so.
Malbim (Melitzah): The Ru'ach tells how it had Shalom with the Yetzer ha'Ra; it did not cease it from Avodas Hashem. Actions done for an end are compared to planting a vineyard.
Where is "Ba'al Hamon"?
Rashi: It is in Yerushalayim, which is Rabas Am v'Hamon Rav. Ba'al is a plain, like "mi'Ba'al Gad b'Vik'as ha'Levanon" (Yehoshua 12:7).
Malbim (Melitzah): Shlomo had a great vineyard, i.e. a multitude of actions, deeds and engagements - both in Chachmah and Da'as, and in good deeds. Therefore, it says that it was in Ba'al Hamon.
What is the significance of giving the vineyard to guardians?
Rashi: He gave it to harsh masters - Bavel, Madai, Yavan and Edom. Midrash Shir ha'Shirim supports that these guards are kingdoms.
Seforno: It is given to Chachamim of the generation.
Malbim: It was to Bnei 1 Yerushalayim - his bodily powers. All of them guarded the vineyard and worked it. Intellectual powers guarded the vines of investigation and ideas. Life forces guarded the clusters of Avodah and Mitzvos.
What is the meaning of "Ish Yavi b'Firyo [Elef Kasef]"?
Rashi: All that [the kingdoms] could collect from [Yisrael] - head tax, tithes, extortion - they collected it all from them, to bring into their houses.
Seforno: This is so everyone will establish many Talmidim, in order that Torah will increase.
Malbim (Melitzah): Everyone received great reward and dear, desired things.
Malbim (Mashal): Shlomo's vineyard was so big that every guard brought to him 1000 silver pieces - the value of his Peros.