He starts from the very bottom of C-Class as a warm-up (duh!) to the top of S-Class, if Hokuto Shinken's 2000-year-old history allows it. Obviously, Saitama is moved at the very end of that gauntlet, and Ken doesn't get to fight King, because we know that even Hokuto Shinken can't do anything against the King Engine , or Blast, because we don't know much about this guy. Ken is fully rested and healed before each fight.
Where does he stop?
Bonus: Same as before, except that Kenshiro now gets to activate Musou Tensei before each fight. How much does it change the gauntlet?