Question One: Should Istikhara be prayed once or multiple times?
Answer:
Assalamu alaikum. When one is not clear about the result of the
istikhara , the fuqaha mention that it is recommended to repeat it, up
to seven times if necessary (usually done on separate occasions).
Getting a Dream After Istikhara?
It is not necessary that you get a dream or even a "feeling". Rather,
the istikhara is a prayer that Allah guide you towards that which is
best (khayr) for you. If you do the prayer of guidance (istikhara)
with the propermanners, the most important of which is to truly
consign the matter to Allah and suspend your own inclinations, then
Allah will make events unfold in the direction that is the best for
your worldly and next-worldly affairs.
In general, when it is not possible to perform the istikhara prayer
itself (suchas when one is out on the road, or in one's
menstrualperiod), it is recommendedto simply read the dua itself.
[Radd al-Muhtar]
The istikhara prayer may be made for a specific matter or be made for
a general seeking of all that is best. Some scholars, including Imam
Abd al-Wahhab al-Sha`rani andIbn `Arafah before him saw this kind of
(specific) istikhara prayer as being superior.
Others, including Shaykh Ibn al-Arabi, recommended performinga general
istikhara prayer for all that is good every day, ideally at the time
of the Duha prayer (after sunrise).
Before Istikhara Prayer
Imam al-Nawawi mentioned that before theistikhara prayer, one should
seek advice (istishara) from those whose knowledge, wisdom, and
concern one is confident.
Ibn Hajar al-Haytami and others mentioned that one of the benefits of
this is to further distance oneself from the desires ofone's own
egotistical inclinations.
Opening the Prayer
It is recommended to open the dua of istikhara [below], with praise of
Allah and sending blessings on the Prophet (Allah bless him & give him
peace), and to close it in this manner, too.
--
- - - - - - -