Is a Muslim is Permitted to Pray Wearing Shoes?
All perfect praise be to Allah The Lord of The Worlds, and may His peace and blessings be upon our Prophet Muhammad and upon all of his family and companions There is no harm for a Muslim to pray wearing shoes or slippers so long as they are pure, since a man asked Anas Ibn Malik: "Did the Prophet (PBUH) use to offer the prayers with his shoes on?" He said: "Yes." Moreover, Ibn Rajab (May Allah have mercy on his soul) said: "Performing prayer wearing slippers/shoes is permissible according the majority of the Muslim scholars." [Fatih Al-Bary,vol.2/pp.274]. And Allah Knows Best.
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.
What is the expiation for breaking fast due to being on a journey, or being sick, or being in a state of menstruation?
No expiation is due on the aforesaid categories, but they are obliged to make up for the missed fast. However, if any of them failed to do so while being able to, and the next Ramadhaan has come, then making up for those days is incumbent on him/her , and paying the ransom as well. And Allah Knows Best.
How should I deal with the whispers of the devil with regard to ablution and purity?
Whispers in ablution are from the devil, and so you should take refuge in Allah from the devil`s evil suggestions that aim to distort the religion. Thus, once an organ is completely pure, don`t question its purity since having whispers doesn`t mean that the purity is invalid as it has already been established.