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.
Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
I underwent a procedure for a molar pregnancy (hydatidiform mole), and after that, the bleeding continued for more than two months, during which I did not pray. Do I need to make up the missed prayers?
If you have previously experienced postpartum bleeding, the duration of the current bleeding is treated the same as your previous postpartum period. Any bleeding that exceeds this duration must be considered irregular bleeding (istihada), and you must make up the missed prayers. If this is the first time, then any bleeding beyond sixty days is considered irregular bleeding. You must perform ghusl, pray, and make up the prayers for the days beyond the sixty-day limit. And Allah Knows Best.
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.