This other question exists, but it doesn't answer my question: Geometric interpretation of the second covariant derivative
I know the Riemann Tensor can be written as the commutator of the second covariant derivative (assuming the connection is torsion-free):
$$R(u,v)w = \nabla_{u,v}^2 w - \nabla_{v,u}^2 w$$
where $\nabla_{u,v}^2 w = \nabla_u \nabla_v w - \nabla_{\nabla_u v}w$ is the "second covariant derivative".
What I'm missing here is the "why". I don't understand the geometrical meaning of $\nabla_{u,v}^2 w$, or why anyone bothered to invent this expression. How was the formula for the "second covariant derivative" invented, and what is its meaning?
I tried drawing some diagrams showing how the vectors are positioned, but they did not bring me much insight. The other question has better diagrams in the answers.
Here is a visualization of $\nabla_u \nabla_v w$:
Here is a visualization of $\nabla_{\nabla_u v}w$: