We've had Jesus, Lord Chaitanya, and Srila Prabhupada who has shared valuable knowledge of God and lead by example of how to serve The Lord with pure devotion. Will there be a time (in Kali Yuga) where the world could experience a spiritual advance being such as the 3 mentioned above?
Yes, there were, there are and there will always be such exemplary people in all time. We just do not have the capability to identify them or they may not be known to all. In Bhagavad Gita, Chapter 7, Verses 16,17, the Lord says
चतुर्विधा भजन्ते मां जनाः सुकृतिनोऽर्जुन । आर्तो जिज्ञासुरर्थार्थी ज्ञानी च भरतर्षभ ॥
O Arjuna, the people, given to good actions who worship me are four-fold. They are, the one in distress, the one who wants security and pleasure, the one who wishes to know (Me), and the one who knows (Me), O foremost in the family of Bharata!
तेषां ज्ञानी नित्ययुक्त एकभक्तिर्विशिष्यते । प्रियो हि ज्ञानिनोऽत्यर्थमहं स च मम प्रियः ॥
Among these, the jnani, always united (to me), his devotion resolved in oneness, is distinguished because I am totally beloved to him and he is absolutely My beloved.
If we take the times after Chaitanya and Prabhupada, there have always been many such personalities, like Ramakrishna Paramahamsa, Bhagavan Ramana Maharshi, Sringeri Jagadgurus like Chandrasekhara Bharati, Abhinava Vidyateertha Mahaswami, Kanchi Paramacharya, Anandamayi Ma, Tridandi Ramanuja Pedajeeyar Swami, Shiridi Sai Baba, Sri Vasudevananda Saraswati or Tembe Swamy and many more people like them.
Even between Chaitanya and Prabhupada there have been many people of such nature. We just have to be able to identify them. These people are jnanis (whether Advaita, Visishtadvaita etc) who dedicated and devoted their whole life to God and Guru.
So people of such stature exist always in all times.