Do you have daughters?: This question may be expressed as a condition by saying “If you have daughters….” Verses 24-25 deal with the subject of daughters.
Be concerned for their chastity: Chastity is literally “body.” Revised Standard Version and Good News Translation interpret this clause to mean “make sure that they remain virgins [until marriage].” Contemporary English Version is similar with “protect her from men.” We could say “protect their purity [or, chastity].”
And do not show yourself too indulgent with them: This is a gross understatement and likely a misinterpretation; ben Sira’s real feelings about daughters will be expressed in 26.10-12 and 42.9-14. This line literally says “and do not let your face shine on them.” This expression is used in a literal sense in Psa 104.15 (103.15 in the Septuagint) of oil placed on the face. Ben Sira uses it in a figurative sense in 36.22a (Revised Standard Version; 36.27a New Revised Standard Version), where New Revised Standard Version has “A woman’s beauty lights up a man’s face.” He also uses it figuratively in 35.9a (Revised Standard Version; 35.11a New Revised Standard Version), where both Revised Standard Version and New Revised Standard Version have “with every gift show a cheerful face.” If he is using the term consistently, what he means here is very close to “and don’t smile at them.” (Read 42.9-14 and you will see that he could very well mean just that.) An American Translation translates this line “And do not look too favorably upon them,” but other ways to express are “Do not let a daughter always have her own way” (Contemporary English Version) and “don’t spoil them.”
Quoted with permission from Bullard, Roger A. and Hatton, Howard A. A Handbook on Sirach. (UBS Helps for Translators). New York: UBS, 2008. For this and other handbooks for translators see here.

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