Which is better, to pray at a prayer place (Musala) whereas many people pray in it, or at a near by mosque in which a few people perform prayer?
Praying at the mosque that has a bigger number is better so long as the number of praying people at the other mosque permits performing prayers in congregation. 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.
Should the Zakah (obligatory charity) giver tell the poor recipient that this is the Zakah of his money?
No, he shouldn`t. But, the Zakah giver should make an intention in his heart that it is the Zakah of his money when paying it to the poor. And Allah Knows Best.
Is Zakah due on the orphan`s money?
Yes, Zakah is due on the money of the orphan.