“Midrashim” about “Baalei Teshuvah,” People who Repented Some of the “Midrashim” found in the Talmud about “Baalei Teshuvah,” People who Repented, are as follows: “One who says, ‘I will sin, then repent; I will sin, then repent’ is not permitted to repent.” (Masechet Yoma 85b)
What happens to somebody who really says to himself, "I will sin then repent, sin then repent," then does exactly so numerous times in a wicked way.
Later on realizes that this was his biggest mistake in life and without a doubt ( He thinks he lost his chance of doing Teshuvah.), feels true genuine regret, begins to live an honest and upright life, is humble to himself and the people around him or her, changes his wicked ways once and for all, tries to repent with full love for Hashem, tries to do teshuvah in all honesty as effectively as possible with full heart, soul and intention, doesn't want to lose the ability to do teshuvah, feels remorse and never returns to the sin again.
Does Hashem have mercy on such a Soul ?