Is the sudden closure of the workplace and an unexpected holiday, after performing Istikhara regarding giving something to two people, considered a deterrent from completing it? Is it permissible to repeat Istikhara? Is one Istikhara sufficient for more than one matter?

The preponderant opinion after performing istikhara (guidance prayer) is that a person should proceed with their matter. If it is good, Allah will facilitate it; otherwise, He will avert it. The described incident is not considered an explicit averting from Allah. There is no harm in repeating istikhara, and it is permissible to perform istikhara for multiple matters with a single prayer, although it is preferable to perform a separate prayer for each matter.