I will consider an observable $\mathcal{O}\in\mathcal{L}(\mathscr{H})$ and, for simple, let me assume $\mathscr{H}$ is finite dimensional. Now, for some time independent hamiltonian $\mathcal{H}$ I can evolve $\mathcal{O}\to\mathcal{O}(t)=U_t^\dagger\mathcal{O}U_t$, where $U_t=e^{-it \mathcal{H}}$. I then define $\delta\mathcal{O}(t)=\mathcal{O}(t)-\mathcal{O}$, which is hermitian for $\mathcal{O}$ is hermitian. Something sounds weird to call this object an observable; I don't see how to represent it in a time independent frame, that is, to the best of my knowledge this can be defined only at the Heisenberg picture.
In this simple, finite dimensional case, does legit quantum observables demand a representation in both Heisenberg and Schrodinger picture? In particular, is $\delta\mathcal{O}(t)$ an observable and, if not, what is the catch?
At a more operational perspective, it also seems to me that acquiring the outcomes of such operator would demand measurements which are non-local in time. So, a related question: is $\delta \mathcal{O}(t)$ measurable? I am aware of cases in which one can assign a two-point-measurement protocol to obtain such outcomes, but I am interested in the general case in which I do not have to assume anything about the state of the system.