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There's a general prohibition to cut down fruit trees (see this question), based on 'bal tashchis'. Would the prohibition apply even to fruit trees that are expensive to maintain (and do not produce enough fruit that would cover the expenses of its upkeep)?

The Mishnah in Kesuvos (8:5) implies that old trees can be cut down, and I assume that commentaries would talk about the issue over there.

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It is only prohibited to cut down trees for no purpose, but what "purpose" includes is hard to define. Rambam Laws of Kings 6:9 deals with your case directly, however:

כל אילן סרק מותר לקוץ אותו ואפילו אינו צריך לו. וכן אילן מאכל שהזקין ואינו עושה אלא דבר מועט שאינו ראוי לטרוח בו. מותר לקוץ אותו.

It is permissible to cut down any non-fruit bearing tree, even if one has no need for it. Similarly, one may cut down a fruit bearing tree that has become old and produces only a slight yield which does not warrant the effort required to care for it.

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    Commented May 27, 2014 at 1:23
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The Gemara in Bava Kamma 91b discusses this:

אמר רב דיקלא דטען קבא אסור למקצציה מיתיבי כמה יהא בזית ולא יקצצו רובע שאני זיתים דחשיבי א"ר חנינא לא שכיב שיבחת ברי אלא דקץ תאינתא בלא זמנה אמר רבינא ואם היה מעולה בדמים מותר תניא נמי הכי (דברים כ, כ) רק עץ אשר תדע זה אילן מאכל כי לא עץ מאכל הוא זה אילן סרק וכי מאחר שסופו לרבות כל דבר מה ת"ל כי לא עץ מאכל להקדים סרק למאכל יכול אפילו מעולה בדמים ת"ל רק

The Gemara discusses a certain amount of fruit that the tree must produce in order to prohibit its being cut down. The Gemara concludes that a tree which is worth more as wood (for building) than the fruit it produces is not prohibited to cut down. This is understood to mean that you can only not cut down a fruit tree when it is wasteful (Rambam Melachim 6:8). Therefore, if it is not a waste, as in this case where it is costing more for its upkeep than it is worth, it would not be prohibited (Rambam ibid halacha 9).

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