What is the meaning of the Prophetic statement that a boy is held in pledge (murtahan) for his 'aqīqah?
All praise is due to Allah, and may peace and blessings be upon our Master, the Messenger of Allah.
The first interpretation: That if the boy dies in infancy without an 'aqīqah having been performed on his behalf, he will not intercede for his parents on the Day of Resurrection. This is the position of Imam Aḥmad ibn Ḥanbal, and Imam al-Khaṭṭābī concurred with him, stating: "The finest of what has been said regarding this matter is the position adopted by Aḥmad ibn Ḥanbal." — [Fatḥ al-Bārī by Ibn Ḥajar,{Vol.9/P.594]
The second interpretation: That the child is likened to a pledged object (marhūn) — one from which full benefit and enjoyment cannot be derived until it is redeemed. A blessing is only made complete upon the one blessed when they fulfil the obligation of gratitude (shukr), and the prescribed expression of gratitude for this particular blessing is what the Prophet ﷺ established as Sunnah — namely, the slaughtering of the 'aqīqah on behalf of the newborn as an act of thankfulness to Allah the Almighty and as a supplication for the wellbeing and safety of the child. This is the position of Mullā 'Alī al-Qārī. See: [Mirqāt al-Mafātīḥ Sharḥ Mishkāt al-Maṣābīḥ, Vol.7/P.2688]
And Allah Almighty knows best.
Can a person required to give kaffarah feed it to their own family members?
The kaffarah must be given to the poor and needy who are not financially dependent on the one giving the kaffarah.
If a person feeds it to their own family members, it does not count as kaffarah, and their obligation remains unfulfilled.
Is it permissible to give multiple mudds (portions) of fidyah to a single person?
Yes, it is permissible to give multiple mudd of fidyah to a single person, because each day of fasting is considered an independent act of worship.
What should a person who was favored from Allah with a newborn, but couldn`t afford an Aqeeqah, do?
Aqeeqah (the sheep slaughtered on the seventh day from the child`s birth) is a desirable Sunnah for the financially able since Allah, The Exalted, charges not a soul beyond its capacity. Therefore, if the father couldn`t afford the Aqeeqah before the end of his wife`s confinement, then it isn`t due on him, and if he was able to afford it later on, then it is permissible, but if he didn`t until the child reached puberty, the latter can offer the Aqeeqah himself.