What is the difference between relying on Allah (tawakkul), seeking counsel (istishara), and hesitating in making a choice, knowing that I always rely (on Allah) and yet I still hesitate and seek divine guidance (istikhara)?

There is no contradiction between a believer's reliance on his Lord in a matter, his seeking divine guidance (istikharah), and his consulting experts. All of these are encouraged by Islamic law. A Muslim should attach his heart to Allah and his limbs to the means (causes). This is the reliance (tawakkul) of the believers. If a Muslim desires something, he should perform the Istikharah prayer, recite its supplication, and consult trustworthy experts. Then, he should rely on his Lord without hesitation, for Allah will facilitate what is best for him.