Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?

It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.

What is the expiation for breaking fast due to being on a journey, or being sick, or being in a state of menstruation?

No expiation is due on the aforesaid categories, but they are obliged to make up for the missed fast. However, if any of them failed to do so while being able to, and the next Ramadhaan has come, then making up for those days is incumbent on him/her , and paying the ransom as well. 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 to give the expiation due on the vow of anger to one person?

The expiation for the vow of anger-and that of the oath-is to be given to (10) needy persons, or a needy family of ten individuals, but giving it to one person is impermissible.