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.
Should a person feel pleased, or have a virtuous vision after offering Istikhara (guidance prayer) in order to do what he/she had offered it for?
The result of the Istikhaarah is not necessarily that a person sees something (in his dream), or feels pleased, but the most important result of the Istikhaarah is whether a person is enabled to do a given matter or not.
What is the ruling of Islamic Law on supplicating with other than the transmitted (Ma'thur) supplications in prayer?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
It is permissible to supplicate (make du'a) during the prayer for anything from the affairs of religion or worldly life, and the prayer is not invalidated by doing so.
Shaykh al-Islam, the Imam an-Nawawi, may Allah have mercy on him, says: "Our madhhab [i.e., the Shafi'i madhhab] holds that it is permissible for a person to supplicate during it [the prayer] with anything that is permissible to supplicate with outside the prayer, from the affairs of religion or worldly life. He may say: 'O Allah, grant me wholesome sustenance, offspring, a house, and a beautiful young wife' — describing her; or: 'O Allah, free so-and-so from prison,' or 'destroy so-and-so,' and other such things — and none of this invalidates his prayer according to us. And this is also the view of Malik, ath-Thawri, Abu Thawr, and Ishaq." [Al-Majmu', Vol.3/P.454]. And Allah, the Exalted, knows best.
I hired a private tutor for my son through an academy that sends teachers [to families] and takes a percentage [of their pay]. At the start of the [new] school year, I arranged directly with that same teacher, without the academy's knowledge. What is the ruling on this?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
The ruling on this matter depends on knowing the specific terms of the agreement and contract concluded with the academy. If the agreement stipulates that no arrangement may be made with any of the students except through the academy itself, then it is not permissible for you to breach the terms of this contract, based on the words of our master, the Messenger of Allah ﷺ: "Muslims are bound by their conditions." (Related by al-Bukhārī)
However, if the agreement pertains only to teaching a specific subject, and the agreement concludes once that subject is finished, then there is no objection to arranging with the teacher to teach other subjects after the contract period has ended, outside of the academy.
Whatever the case maybe, the teacher must uphold the terms of his contract with the academy. And Allah, the Exalted, knows best.