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It is good to follow the advice of the Istekhara. Wassalam 

Istekhara is not obligatory in every situation. Istekhara is seeking guidance when you are unable to decide. If the matter was clear for you, then there is no need for Istekhara. Unnecessary Istekhara is not binding.

'Wassalam.

You do not need to perform istikhara prior to vacation. In fact, it is probably better not to do so, unless you have some uncertainty.

The Istekhara is valid as far as the circumstances of the matter has not changed. 
'if the matter has changed then another Istekhara can be seen.Wassalam.