Crybaby Son

My step-son really “FEELS” his feelings. He’s 6, and I love him to death. He’s very emotional, and anytime something doesn’t go his way, he cries. If he thinks he’s in trouble, he cries. He’s tired, he cries. Time to do homework, he cries.

My model..
C: Son crying
T: He would be better off if he was stronger.
F: Worry
A: Scold him for crying
R: keeps crying

C: Son crying
T: This is inappropriate for a child his age.
F: Frustration/worry
A: Tell him crying is not an appropriate reaction. Tell him there is no need to cry. Tell him to tell himself “I’m okay”
R: he still cries.. or maybe it lessens

Should I just let him “feel his feelings” or try to correct this? And how do I help him not be a crybaby without suppressing his emotions?