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 it permissible for a suitor to go out with his fiancé upon the conclusion of the marriage contract?
Upon the conclusion of the marriage contract, the woman becomes lawful for her husband. However, the customary practice should be observed in this regard since rights could be lost in case of divorce, or death.
Is permissible to buy/sell with non-Muslim?
Yes buying/selling for a Muslim with non-Muslim is permissible as regards what is lawful.
Is it permissible for a woman to visit the doctor while in her `Iddah (waiting period)?
It is permissible for her to do that during day time, but it is impermissible for her to leave her house at night except for a sound reason. And Allah Knows Best.