Suppose that $x, y \in \mathbb R^n$ are different points of the $n$-dimensional Euclidean manifold. Let $u \in T_x \mathbb R^n$ and $v \in T_y \mathbb R^n$ be tangent vectors in the two different fibres.
We usually treat them as members of the same vector space $\mathbb R^n$, so that we can take the sum $u+v$ and the difference $u-v$.
I would like to understand this from the differential geometry point of view, in particular with respect to "connections".
A connection over a smooth manifold defines, among other things, the transport of a tangential vector along a path. So when I calculate $u + v$, then I am actually transporting, say, $u$ along a path from $x$ to $y$ and compute the sum in the tangential fibre at $y$.
From the differential geometry point of view, what feature ensures that the transport is path-independent?
Is the transport of tangent vectors always reversible, that is, does transporting forward and then backward yield the original vector?
For the Levi-Civita connection on a Riemannian manifold, the parallel transport will be path-independent if the curvature vanishes. For surfaces this would be Gaussian curvature; for higher-dimensional manifolds, the sectional curvature. This is true if the manifold is simply connected; otherwise, require the paths to be homotopic (with fixed endpoints). Parallel transport along a given path is always reversible in the sense you mentioned.