|Bismillahir Rahmaanir Raheem
Al Jawaab Billahit-Tawfeeq
1) It is best for the person seeking divine guidance to perform Istikharah him/herself since the words of the Hadeeth indicate the same.
According to a traditional report transmitted on the authority of Muhammad ibn al-Munkadir, it was Jabir ibn ‘Abdullah who said: “Allah’s Messenger used to teach us how to seek guidance in choosing the best option available in a practical enterprise [al-Istikhara Fi’l-Amr], just as he would sometimes teach us a Chapter (Surah) from the Qur’an:
“If one of you is concerned about some practical undertaking, or about making plans for a journey, HE should perform two cycles (rakaats) of ritual prayer, not as an obligatory observance (Fardh), but voluntarily (Nafl). Then he should say:
Allahumma inni astakhiruka bi ilmika wa-astaqdiruka biqudratika wa-as’aluka min fadhlika al-adheem. Fa innaka taqdiru wala’ aqdiru. Wa ta’lamu wala a’alamu wa anta allaamul ghuyub. Allahumma in kunta ta’lamu anna [hadhal-amr] khayrun li fi deeni wa-ma’ashi wa-aqibat amri, fa’qdruhli wa-yasirh li thumma barik li feehi. Wa in-kunta ta’lamu anna [hadhal amr] sharrun li fi deeniy wa-ma’ashi was-‘aqibat amri. Fa asrifh anni wa-srif ‘anhu. Wa aqdurh liyal khayr hayth kana thumma a-rdhini bihi
Translation: O Allah, Behold I ask You the good through Your Knowledge, and ability through Your Power, and beg (Your Favour) out of Your infinite Bounty. For surely You have Power; I have none. You know all; I know not. You are the Great Knower of all things. O Allah! If in Your Knowledge [this matter] be good for my faith (Deen), for my livelihood, and for the consequences of my affairs, then ordain it for me, and make it easy for me, and bless me therein. But if in Your Knowledge, [this matter] be bad for my faith (Deen) for my livelihood, and for the consequences of my affairs, then turn it away from me, and turn me away there from, and ordain for me the good wherever it be, and cause me to be pleased therewith.
NOTE: It has become somewhat of a norm for people to ask pious elders to perform Isitkharah on their behalf. Although permissible, majority of the Ulamaa discourage this since the actual Sunnah is to perform Istikharah yourself. The Prophet (sallallahu ‘alayhi wasallam) was the most inspired and most pious of mankind, yet there is no mention of any incident where a Sahaabi would have asked him to perform Istikhaarah on his behalf. People generally prefer to ask others because they feel their inclination could be biased. However, if one asks for divine guidance with utmost sincerity, not just in order to get the nod to whatever it is he wants, then Allah will most certainly inspire him to take the path that is best for him.
2) Isitkhaarah should be performed for seven consecutive nights. If no inclination is felt, then it should be continued for a farther seven days, and if confusion prevails even after the 14 days, it can be done up to 21 days.
3) That would mean that the issue at hand is good for one party but not for the other.
And Allah knows best
A. Z. Pandor