What is the relationship between the outcome of Salatul-Istikhara and Allah's pleasure with His servant, and does repeated failure after Istikhara mean Allah's displeasure or a misjudgment of the matter?

The reality of Istikhara is the servant entrusting their affairs to Allah the Almighty, for Him to choose what is best for them. The feeling of contentment in one's heart is not a definitive sign of its outcome. Rather, what is required of the servant after performing Istikhara is to proceed with the matter, and success or lack thereof is the result of the Istikhara. Lack of success does not signify Allah's displeasure; rather, it might be what is best for the servant. Steadfastness and obedience are always required. Distinguishing between striving diligently and insisting on something that Allah has not decreed is a matter of the unseen. Exerting effort is required, and the servant entrusts their affairs to Allah. If they are not successful, there is wisdom in that, and they must submit and be content with Allah's decree, for what a person dislikes may be good for them.