Why did Avraham give Hagar only bread and water, but no money?
Rashi: Because he now hated him for having strayed from the right path. 1
Ramban (to 21:15): Because Sarah ordered him to do so, and HaSh-m instructed him to comply. 2
Chizkuni: Avraham and Yishmael were both converts, and the Gemara states in Kidushin 17b that converts do not inherit each other, even mi?de'Rabanan. 3
Rabeinu Bachye: Through prophecy, Avraham knew that Yishmael's descendants would oppress Yisrael, and the Pasuk writes in Mishlei 25:21 "Im Ra'ev Sona'acha Ha'achilehu Lechem, ve?Im Tzamei Hashkehu Mayim".
Kol Eliyahu: A Midrash learns from here that Avraham's house were Vatranim (very generous). This is astounding! Rather, Da'as Torah is that eating is more than drinking (Megilah 12a). It says in Avos (6:4) to eat [as much as you want of bland] bread with salt, and drink water bi'Mesurah (a tiny measure). Normally, one drinks in a Kad (small flask). Avraham gave Chemas Mayim (a large pouch).
Radak: He also gave money, just the verse did not mention it. Surely he did not send them empty-handed!
Ohr Yechezkel (Darchei ha'Avodah, p. 174): Even though Yishmael was sick, now Avraham needed to use the Midah of cruelty.
It is difficult to understand the difference in Avraham's reaction towards Yishmael and his reaction to Sedom (who did not stray any less than Yishmael). Refer to 21:14:1:2*.
Which explains why he did this in spite of the fact that it went against every fiber of his being (the greatest Ba'al-Chesed who ever lived).
In fact, the Chachamim are displeased with one who returns a loan to a convert, the son of the lender [in case people say that they are Halachically related]. He did however, intend to give him gifts after Sarah died, like he gave to the Bnei ha'Pilagshim.
Did Avraham place Yishmael (who was at least 16 years old) on Hagar's shoulders?
Rashi: Yes. Sarah gave Yishmael an Ayin ha'Ra, and he became feverish, unable to walk by himself. 1
Ramban: The words "v'Es ha'Yeled" belongs earlier, after "El Hagar." In other words, Avraham put bread and water on her shoulder, and gave to her Yishmael, to accompany her wherever she went.
Gur Aryeh: How is this derived? The verse could have said, 'and he gave her the child.' It says, "and the child' without specifying; referring to the previous phrase.
Why does the Pasuk see fit to add that he placed the bread and water on her shoulders?
Targum Yonasan: It hints that he also tied them 1 to her loins, as a sign that she was a slave.
Peirush Yonasan adds that he tied a veil to her loins.
What does the Torah mean when it says that "she strayed in the desert"?
Rashi: It means that she reverted to the idolatry of her father's house. 1
Rashbam, Targum Onkelus and Targum Yonasan: She literally lost her way and strayed in the desert of Be'er Sheva.
Gur Aryeh: Why doesn't Rashi explain simply, that she strayed and wandered about, lost? If HaSh-m later opened her eyes and brought forth a spring of water (21:19), certainly He would send (in Avraham's merit) an angel to lead the way, and prevent her from wandering! Rather, the verse means that she reverted to idolatry.
QUESTIONS ON RASHI
Rashi writes: " He placed even the child on her shoulder." But Yishmael must have been at least seventeen years old?
Gur Aryeh (to 21:9): Refer to 21:10:1.1:1; refer to 21:10:1.1:2.
Rashi writes: "Fever took hold of him, and he was unable to walk." But the Gemara (Bava Metzia 87a) teaches that until Yaakov's time, no one experienced weakness [due to illness]?
Mizrachi, Da'as Zekenim (to 21:15): Until Yaakov, no one fell sick due to a Heaven-sent illness. Yishmael became sick due to Ayin ha'Ra, which is caused by a person (akin to striking with a sword).
Gur Aryeh: While there was no weakness (Chulshah) prior to Yaakov, there was pain. This is comparable to two warriors struggling against each other - neither is knocked down, but each feels pain and stress due to his combatant. Illness at that time in history involved the pain and fever caused by opposing forces within the body. Since Yaakov's time, however, a person does feel "knocked down" due to illness. 1
See Gur Aryeh as to why this began with Yaakov Avinu.
Rashi writes: "Fever took hold of him, and he was unable to walk." But the Gemara (Bava Basra 16b) teaches that HaSh-m blessed Avraham with a precious stone with healing properties, which he wore around his neck, and whoever saw it would be healed?
Gur Aryeh: Healing would not come with one glance; rather, the patient had to continue to gaze at the stone until fully healed. Yishmael was now leaving Avraham, and therefore could not avail himself of this method.