Who is "Ish Machsor Ohev Simchah"?
Rashi: It is one who loves the Simchah of constant partying.
R. Yonah: He is a man who lacks. If he is wealthy, poverty will come to him from this Midah. Ohev Simchah is like "v'Hinei Sason v'Simchah Harog Bakar v'Shachot Tzon" (Yeshayah 22:13), "Lischok Osim Lechem v'Yayin Yesamach Chayim" (Koheles 10:19). Above (verse 15) discussed a Tzadik's Simchah in Avodas Hashem; here discusses the lowliness of Simchah in pleasures. It scorns them based on worldly matters; the person will come to lack. However, there are [also] other reasons to scorn it. (a) He makes this world primary when he delights in its follies, and he is drawn after physicality via pursuing pleasures. (b) According to his Simchah in pleasures, so will be his sadness in abandoning them. Also, he might lose his wealth via an evil mishap. According to his initial Simchah, so will increase his agony later. (c) Rejoicing over something that ceases shows his folly - "ul'Simchah Mah Zo Osah" (Koheles 2:2), "Im Esmach Ki Rav Cheili" (Iyov 31:25).
Malbim: Simchah will not be constant. Anything that he delights in when he first gets it, after he sees it, or owns it for some days, he ceases to rejoice over it. He wants to see in place of it something new to make him rejoice; he is always lacking.
Why will one who loves wine and oil not become rich?
R. Yonah: One who is drawn after drinking wine and pleasurable foods, he accustoms his limbs to rest. He will come to view rest as good, and flee from exertion. When he will get to the Midah of laziness, he will sink in the depth of poverty, for it makes Ba'aleha (those who have the Midah) poor - "u'Va chi'Mehalech Reishecha" (6:11).
Malbim: He loves to drink and rejoice his flesh with delicacies. Not only will he lack - he will deplete his money. If he merely loves Simchah, he need not deplete his money.
