Should a prayer performer who forgets to offer the middle Tashahod (saying ash-hadu anala ilaha ila-alah) offer Sujood As-Sahw (prostration of forgetfulness)?
He/she should offer two prostrations of forgetfulness at the end of the prayer. And Allah Knows Best.
When is Istikharah (guidance prayer) Du`a offered, before Tasleem (saying asalamu alikum warahmatu allah wa barakatuh to end the prayer), or after it?
It is offered after Tasleem.
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.
Is Making up Missed Obligatory Prayers an Obligation?
All perfect praise be to Allah, The Lord of The Worlds, and may His peace and blessings be upon our Prophet Muhammad and upon all of his family and companions.
Missed obligatory prayer/prayers is a debt upon Muslim and making it up is an obligation, since the Prophet (PBUH) said: "pay the debt due to God, for it is the one which most deserves to be paid." [Agreed upon]. And Allah Knows Best.