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.
I work in an accounting and auditing office, and among the clients of the office are restaurants, hotels, and supermarkets that sell alcohol. Our work is limited to collecting invoices, whether purchases, sales, or expenses, and recording them in daily books. We also review income and sales taxes on behalf of these clients.
You are more knowledgeable about the nature of your work. If you see it as assisting in wrongdoing, then it is forbidden, as Allah The Exalted Says (What means): "And cooperate in righteousness and piety, but do not cooperate in sin and aggression" [Al-Ma’idah/2]. However, if your work is merely documenting the reality, then I hope there is no sin upon you. The the pious predecessors (Salaf) used to take the tithe from the traders of the People of the Book, even if it included alcohol, after knowing the value of their goods. And Allah The Almighty Knows Best.
What is the ruling on training dogs that are of benefit?
All perfect praise be to Allah the Lord of the Worlds. May His peace and blessings be upon our Prophet Mohammad and upon all his family and companions.
This is permissible because Allah The Almighty Says (What means): "They ask thee what is lawful to them (as food). Say: lawful unto you are (all) things good and pure: and what ye have taught your trained hunting animals (to catch) in the manner directed to you by Allah. eat what they catch for you, but pronounce the name of Allah over it: and fear Allah. for Allah is swift in taking account." [Al-Ma`idah/4]. However, it is prohibited to keep dogs for no benefit because Salim reported on the authority of his father that Allah's Apostle (PBUH) said: "He who kept a dog other than one meant for hunting or for watching the herd, lost two qirat of his reward every day." [Moslim]. And Allah The Almighty Knows Best.
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.