For those that design their own parts, about how many iterations do you usually print up test pieces to make sure your design works?

For me, fourth time is the charm here. Even that, there is one change that I really should do but its not necessary. I recently got a CMF Watch Pro 2, and I wanted to design a charging dock for it that fits the magnetic charge cable snugly, and also that if I'm traveling I can wrap the cord neatly around the back. What do you all think?