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.
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.
Is wearing a cap permissible for boys, or girls?
All Perfect Praise is due to Allah, The Lord of The Worlds.
In principle, anything is permissible sol long as there is no Sharia evidence prohibiting it, thus wearing the cap by boys is permissible as long as it isn`t done in imitation of the disbelievers. Moreover, a Muslim woman should avoid all that which attracts the attention of men because whatever leads to the forbidden is forbidden. And Allah Knows Best.
Is it permissible for one to shake hands with his uncle`s daughter?
No, it isn`t because he is a non-Mahram (Marriageable) to her.