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.

What should a person, who doubts the validity of his Wudu, or over performs it, do?

One who doubts the validity of his/her Wudu while performing it should redo it until he/she is certain of having attained purity. But, if doubt was after having performed Wudu, then he/she should not pay attention to that as doubt after the end of an act of worship does not count. This is of course in case doubt was within the reasonable limits since once it goes beyond that, it becomes a whispering of the Shaytaan (devil) which he/she should ignore as the Wudu is valid.

A man break his fast once during Ramadan and he already have an expiation of fasting for two consecutive months. He fasted for a month and passed away. Is it permissible for his sons to fast the remaining month equally? 

Does passing wind from the anus affect ritual purity?

Ablution is nullified by the passing of wind from the anus, but washing the anus is not required as wind leaves no impurity.