Is it permissible for the guardian to give Sadaqa (voluntary charity) from the money of the orphans?

It is impermissible for the guardian to donate from the money of the orphans because he is entrusted with the safekeeping of that money, and is prohibited from donating it.

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 my brother, whom I had suckled, to conclude a marriage contract between his daughter and my son?

Such marriage is impermissible since one`s nephew in this situation is considered an uncle to one`s daughter; consequently, he is the brother of her father by suckling. In such cases, the people in question should go to court to prove the suckling.

What is the ruling on praying behind an undesirable Imam?

It is permissible to pray behind an Imam who is undesirable for committing religious violations, and it is disliked for such an Imam to lead the prayer. Still, If he was undesirable for a personal, or a worldly matter, then such argument doesn’t hold water. And Allah Knows Best.