I guess I'm stumbling because if I start with an abstract cochain $\phi$ of $C^n(X; \pi_n F)$ and take $\delta \phi$ it might not have any geometric meaning because $\phi$ doesn't have any geometric meaning because it has nothing to do with obstruction
The context of the section and stuff is not relevant anymore
Maybe we could work out an example of a bundle where it's not a coboundary
Uhh, what's a simple example of a fiber bundle over a 2-complex with no sections, but which trivializes over the 1-skeleton?
So, give $S^2$ the cell structure of a circle with two disks attached (northern/southern hemispheres). Call this cell complex $\mathscr{S}$.
$\mathscr{S}^{(1)}$ is merely $S^1 \subset S^2$ (:P @ notation), and the bundle $E = T_1 S^2$ over $\mathscr{S}$ trivializes over $\mathscr{S}^{(1)}$.
Take a section $s : \mathscr{S}^{(1)} \to E$ which is the constant unit vector along the equator.
There are two 2-cells $e_1, e_2$ of $\mathscr{S}$. From the way we defined the obstruction cochain $\psi \in C^2(\mathscr{S}, \pi_1 F)$, $\psi(e_1)$ is (because the attaching map of $e_1$ is just the identity map $S^1 \to \mathscr{S}^{(1)} = S^1$) just the section $s : \mathscr{S}^{(1)} \to E$, homotoped inside the fiber $F$ (which is again a circle)
If I am not wrong, the unit tangent vector along the equator of the sphere, as free loop in $T_1 S^2 = SO(3)$, homotopes to the generating element of $\pi_1 F$
Think of shrinking the equator to the north pole. Then it's unit tangent vector field shrinks to the fiber $F$ over it
So $\psi(e_1)$ is the generator $1$ of $\pi_1 F = \Bbb Z$. Similarly $\psi(e_2)$ is $-1$. Then that cochain $\psi \in C^2(\mathscr{S}, \pi_1 F) = C^2(S^2, \Bbb Z)$ is precisely the top dimensional cellular cochain representing the generator of $H^2(S^2)$, so not the coboundary
No, $\psi(e_2)$ is $1$ again. No difference happens in that computation, 'cuz the attaching map of the bottom cell is still via identity.
I was really scared because $\psi(e_1) = 1$ and $\psi(e_2) = -1$ would have actually meant it was $\delta \phi$ where $\phi \in C^1(S^2; \Bbb Z)$ takes $\phi(S^1) = 1$ on the equator $S^1 \subset S^2$.
(I hope I am right on the sign issues)