Reference: Fataawa wa Rasaa.il Shaykh ‘Abdur-Razzaaq ‘Afeefee – Page 410, Fatwa No.14
Question: Is it correct to pray the two rak’ahs for the istikhaarah [prayer] for two separate issues?
Response: You should pray two rak’ahs for the istikhaarah [prayer] for something specific, then you should pray [another two rak’ahs for] the istikhaarah [prayer] for another matter; This, also being in addition to the [istikhaarah] supplication, and two rak’ahs [for the istikhaarah prayer] are not sufficient for two separate issues.