Is it permissible for a man to wear transparent clothing?
It is not permissible for a man to wear transparent clothing that reveals his 'Awrah (the area that must be covered). The 'Awrah of a man is "from his navel to his knees", and modesty is more prudent. 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.
Is Iddah (waiting period) incumbent on an old woman whose husband had died?
Upon the death of the husband, Iddah is incumbent on the wife regardless of their age. 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.