What is bad if one must buy grain each year?

Rashi: He worries lest he not have money to buy grain next year.

Maharsha: This is among the curses, for when Yisrael were on their land, every Jew had land. After they were exiled, they lacked land to seed. Rashi on Chumash brought the Drashos from the Reisha and Seifa, but not from the middle "u'Fachadta Laylah v'Yomam." This is because he brings Drashos close to the simple meaning. Chayecha in the Reisha and Seifa properly refer to grain, which is man's vitality. "U'Fachadta Laylah v'Yomam" does not refer to grain based on simple meaning.

Iyun Yakov: We say (Bava Metzi'a 59) that a man quarrels with his wife about grain - "Re'eh Chayim Im Ishah." One should seed and not buy, even though the cost is the same - the former is blessed (Yevamos 63).

Anaf Yosef citing Yefe Mar'eh: Here it implies that it is better to buy food for many years (and not each year), due to fear of hunger. This seems like a lack of Bitachon! One who has what to eat today, and asks 'what will I eat tomorrow', he has little Emunah. The One who created his day, He created his income (Mechilta, Tanchuma)! I answer that that refers to Hash-m opening His hand to give to everyone what he lacks. For this, one should trust in Hashgachah Pratis for Yisrael. However, food being found in the world depends on the majority - the world is judged based on the majority. One should fear lest the entire country be stricken, e.g. lack of rain, locusts, crops being stricken... Even though it says "b'Ra'av Padecha mi'Maves", we do not rely on miracles. Alternatively, the Midrashim teach that one should not be pained and afraid about matters outside of his control. One should do what he can and not rely on miracles - "b'Chol Mishlach Yadecha Asher Ta'aseh." One who does not prepare himself to receive Hash-m's influence, in what he could do, he causes the influence and Divine help to be lessened.

Etz Yosef citing Yefe To'ar : Even if he is rich, he fears lack of rain, locusts, crops being stricken, and no grain will be sold. The little that will grow, the land owner will keep it for himself.

Why is one who buys bread each day from a baker the worst?