After having said "Lo Se'anun", why does the Torah repeat "Im Anei Se'aneh Oso"?
Seforno: To teach us that the prohibition is confined to where one afflicts them in order to hurt them, but not if one does so in order to chastise them and to guide them on the right path. 1
Hadar Zekenim (in Pasuk 21): As if to say 'If you want to be afflicted, afflict them, because perhaps he will cry and I will hear it, and be angry ... '.
In which case it is even a Chesed to do so (Seforno). See also Ba'al ha'Turim.
Why does the Torah use the double Lashon "Im Anei Se'aneh. "?
Mechilta #1: To teach us that Hashem will hear their cries, 1 irrespective whether the Inuy is a major one or a minor one. 2
Mechilta #2: To teach us that Hashem will only intervene if one transgresses twice.
Why does the Torah use the double Lashon "Shamo'a Eshma be'Kolo"?
Mechilta: To teach us that Hashem will answer them whether they cry out or not - and the Torah mentions "Tza'ok Yitz'ak because He will answer quicker if they cry out. 1
It is not clear however, as to why the Torah repeats the words "Shamo'a Eshhma be'Kolo"?
Why does the Torah not spell out the punishment of someone who afflicts a widow or an orphan?
Rashi: The Torah tends to issue a threat and to leave the punishment unsaid. 1
Ramban: Translating the word "Ki" to mean 'Im' (if), 2 the Torah is saying that if one afflicts a widow or an orphan, then, when they cry out to Hashem, He will answer their prayers. Moreover, whereas others in the same situation require additional effort, Hashem will answer them as soon as they turn to Him, without any effort on their part. 3
As it does with Kayin in Bereishis, 4:15 (See Ramban's objection to both Rashi's explanation and his proof).
Which it writes twice for emphasis (Ramban).
To counter the notion that one can exploit him, because he has nobody to whom to turn for help him (Ramban). The Ramban cites a number of Pesukim which convey the same concept. See for example, Mishlei, 22:22-23 & 23:10-11).
QUESTIONS ON RASHI
Rashi writes that the Torah left the punishment unsaid. But the Torah writes 'I will kill you, and your wives will be widows ... !'?
Riva, Rosh, Moshav Zekenim #1 and Hadar Zekenim (in Pasuk 21): That is only if the afflicted party cries out to Hashem. If they do not, the Torah leaves the punishment unsaid.
Rosh (citing R. Shmuel ha'Kohen) and Moshav Zekenim #2: Rashi means that the Torah did not teach us the punishment for the one who cries out - because if someone is able to go to Beis Din, and asks Hashem to judge, he is punished first (Bava Kama 93a). 1
Moshav Zekenim #3: Rashi means that the Torah did not state the punishmen immediately - It interrupted with "If he will cry out ..."
Also his punishment was taught! The Gemara there learns from "Eschem" (plural) that Hashem will kill also the one who cries out! (PF)
