Yes, this can be proved.
Let me first discuss this in the classical case, and then give you pointers to where you can learn more about the quantum case.
You first have to be careful, when writing down your expectations, to specify the state with respect to which you are actually computing the expectation. In this respect, the physicists' habit of denoting expectation simply by generic brackets $\langle \cdot \rangle$ is very bad. There is no problem for your "double limit" expectation (provided you let $h\to 0$ using positive values only), but the expectation in your "long-range order" case is ambiguous and results actually depend on what it is supposed to mean.
Indeed, when a first-order phase transition occurs (which is precisely what you are interested in), there are infinitely-many different Gibbs measures describing your system in the thermodynamic limit. The set of all such measures is always a simplex, that is, a convex set such that each element can be written in a unique way as a convex combination of extremal elements, the latter being those that cannot be decomposed in a non-trivial way. In the Ising model, for instance, the (translation invariant) extremal measures are those corresponding to the usual $+$ and $-$ phases. In a sense, the only physically relevant measures are the extremal ones, the other describing statistical mixtures and thus not containing any additional interesting physics.
The first statement is then that a measure is extremal if and only if it is mixing. The latter means precisely that the expectation of the product of any pair of local observables $\langle \mathcal{O}(r) \mathcal{O}(r')\rangle$ converges, as $|r'-r|\to\infty$ to the product of the expectations $\langle \mathcal{O}(r) \rangle \langle \mathcal{O}(r')\rangle$. Note that this is an "if and only if" statement, so the claim fails if the state you are considering is not extremal (for example, it fails for the Ising model if you consider the state obtained using free or periodic boundary conditions and zero magnetic field).
As for the second part (with the "double limit"), the point is that by taking this limit (with $h\downarrow 0$, that is, $h\to 0$ using positive values only) you are reaching (in the limit) precisely the extremal state under which the observable has largest expected value. For example, if you take the limit $h\downarrow 0$ in the Ising model, you will get the expected value of the observable under the $+$ state.
The equivalence you want thus immediately follows if the state you use for the "long-range order" is the state you get by letting $h\downarrow 0$ in the "double limit".
The above statements are standard and can be found in several places, among which our book, Georgii's book or Simon's book.
Similar claims also hold in the quantum case. Precise statements and proofs can be found, for instance, in Chapter IV of Simon's book.