Let $X$ be a scheme (a curve over a field for example). Exactness of a sequence $\mathcal{F}\to \mathcal{G}\to \mathcal{H}$ of $\mathcal{O}_X$-modules can be checked on stalks : it is exact if and only if $\mathcal{F}_x\to \mathcal{G}_x\to \mathcal{H}_x$ is exact for every $x\in X$.
If $0\to \mathcal{F}\to\mathcal{G}\to\mathcal{H}\to 0$ is split exact, then so are each of the $0\to \mathcal{F}_x\to \mathcal{G}_x\to \mathcal{H}_x\to 0$, but the converse isn't necessarily true I think.
My question is this : are there useful ``local'' or other criteria (or maybe an obstruction theory of some sort) for checking split exactness of sequences of $\mathcal{O}_X$-modules?
I don't think local is way to go here, because being split on the level of the whole sheaf tautologically requires the existence of a global section to the surjection.
However that's exactly what $Ext^1 (\mathcal{H}, \mathcal{F})$ is for (your obstruction theory if you wish). Split exact sequence corresponds to $0$ element in the Ext group. You can use full force of homological algebra to check it. In particular, since you were interested in the possibility of the local answer, often you can utilize the local-to-global spectral sequence: $$H^q(X, \mathcal{Ext}^p (\mathcal{H}, \mathcal{F})) \implies Ext^{p+q}(\mathcal{H},\mathcal{F}).$$