Is the son of the sister by breastfeeding considered a mahram in Islam, and is it permissible for a woman to go for Hajj with him?
Everything that is prohibited by lineage is also prohibited by breastfeeding. The son of the sister by breastfeeding is considered a mahram, just like the son of the sister by blood, and it is permissible for him to be her mahram for Hajj and Umrah. And Allah Knows Best.
Is it valid for the 'aqīqah to be performed using the newborn child's own wealth?
All praise is due to Allah, and may peace and blessings be upon our Master, the Messenger of Allah.
It is not permissible for the guardian to perform the 'aqīqah using the newborn child's own wealth, because the 'aqīqah is a voluntary act of giving (tabarru'), and a guardian is prohibited from making voluntary expenditures from the child's wealth. Should he do so, he becomes financially liable for what he spent. And Allah Almighty knows best.
Is the father a Mahram (Non-marriageable) to his son`s mother-in-law?
The father is a non-Mahram (Marriageable) to his son`s mother-in-law, so it is impermissible for them to look at each other, or to have a seclusion (Khalwah).
What is the Du`a (supplication) of Istikhara (guidance prayer)?
O Allah, I consult You as You are All-Knowing and I appeal to You to give me power as You are Omnipotent, I ask You for Your great favor, for You have power and I do not, and You know all of the hidden matters. O Allah! If you know that this matter (then he should mention it) is good for me in my religion, my livelihood, and for my life in the Hereafter, or he said: "for my present and future life" then make it (easy) for me. And if you know that this matter is not good for me in my religion, my livelihood and my life in the Hereafter, or he said: "for my present and future life" then keep it away from me and take me away from it and choose what is good for me wherever it is and please me with it."