The question misinterprets the comments of Elon Musk, who is trying to set expectations appropriately.
That is, this is a new vehicle, and there are issues that are next to impossible to model on the ground, nor test on the ground.
They have tested and planned for everything they can, but they accept there is complexity for which they cannot prepare.
So is this poorly designed? No, it is designed by some of the best rocket engineers in the world. (Demonstrably so — developed a new engine, Merlin, through 4 or 5 major iterations (1A → 1B → 1C → 1D → final build), developed a booster through multiple iterations (Falcon 9 Block 5 is due soon, from the 5 you can infer a number of previous iterations). Then they added on recoverability and reusability. Amazing stuff.
They have built a reusable capsule that has flown 14 times, and 2 have been reflown. Amazing stuff.
Yet, even so there is complexity that they cannot predict with complete confidence.
Now there is a different kind of confidence, not in practical things (have we covered all possible launch issues?) but economic confidence, where the actual performance of some physical things does not match with the economic reactions. (Ever see a company come in with higher earnings than expected and yet somehow tank its stock?)
Musk is trying to set expectations appropriately. This is a new booster. It is very complicated. They are as sure as they can be it will work. They are also sure there may be things they missed or could not test.
Thus this is really a test flight, and if it fails, they shall test again. If that fails, again shall they test until they succeed.