The start of the rainy season in the Land of Israel is immediately after Sukkos (see Shulchan Aruch Harav 117:1). Yet, we wait fifteen days before starting to pray for rain, allowing for the last of the pilgrims to Jerusalem for Sukkos to arrive home without getting caught in the rain.

Besides for being a tremendous sacrifice, delaying the prayers for rain, which is necessary for the growth of the staples of human and animal sustenance, raises some Halachic issues as well. Prayer is a mitzvah commanded in the Torah: to petition G-d for all our needs. If we need rain already from Sukkos, how can we not be asking for it? Additionally, the Torah prohibits us from intentionally inflicting pain upon ourselves. How can we knowingly cause ourselves the pain of the crops being possibly delayed due to the late start of the rainy season?

From here we see the extent to which the Jewish people are connected and beloved to one another. Knowing the discomfort that another Jew could suffer due to the rain, all other members of the Jewish community felt that rain before the 7^th of Cheshvan was not a need or benefit but a source of displeasure!

You are only obligated to pray for that which you feel that you need. Similarly, the prohibition of inflicting pain does not apply in instances where the pain is soothing. (For example, fasts that one accepts upon himself as part of his Teshuva are not considered self-inflicted harm, as refraining from food or drink in this instance would be beneficial.) Thus, the delay of the prayer for rain was not only because the community was willing to forego their need for rain in order that another person should stay dry. Rather, the love of one Jew to another is so great that until we are sure that the traveling Jews could be safe at home, the entire Jewish community feels no desire or need for rain at all!

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—Hisvaaduyos 5746 vol. 1, pp. 506-510