Is it permissible to repeat the Istikhara (seeking guidance) prayer, and is it a condition that one should sleep after offering it?

All perfect praise be to Allah,The Lord of The Worlds                                                                                                                                                            Istikhara is offered once, but it is permissible to repeat it, and sleeping after offering it is not a condition for its validity. And Allah Knows Best.

What should a person who was favored from Allah with a newborn, but couldn`t afford an Aqeeqah, do?

Aqeeqah (the sheep slaughtered on the seventh day from the child`s birth) is a desirable Sunnah for the financially able since Allah, The Exalted, charges not a soul beyond its capacity. Therefore, if the father couldn`t afford the Aqeeqah before the end of his wife`s confinement, then it isn`t due on him, and if he was able to afford it later on, then it is permissible, but if he didn`t until the child reached puberty, the latter can offer the Aqeeqah himself.

Is it permissible for the big brother to force his sisters to wear Hijjab (Islamic wear) if their father didn`t do his part in this regard ?

All Perfect Praise is due to Allah, The Lord of The Worlds

The father`s attention should be drawn gently and politely, and the sisters should also be reminded with good words since Allah, The Almighty, Says (What means): "O ye who believe! Save yourselves and your families from a Fire whose fuel is Men and Stones." [Al-Tahreem/6]. And Allah Knows Best.

Is it permissible to make up missed prayers at the times in which praying is disliked?

All perfect praise be to Allah,The Lord of The Worlds                                                                                                                                                                        It is permissible to make up missed prayers at any time even that in which praying is disliked. Absolute supererogatory prayer is forbidden to be performed at the times in which praying is disliked, and this also applies to Ihram and Istikhara prayers. However, there is no harm in offering prayers in Mekah during those times. And Allah Knows Best.