We prove that every closed orientable surface S of negative Euler characteristic admits a pair of finite-degree covers which are length isospectral over S but generically not simple length isospectral over S. To do this, we first characterize when two finite-degree covers of a connected, orientable surface of negative Euler characteristic are isomorphic in terms of which curves have simple elevations. We also prove an effective version of this result, weakening the hypotheses to consider curves with explicitly bounded self-intersection number. We further show that for sufficiently large N , the set of unmarked traces associated to simple closed curves in a generically chosen representation to SLN (R) distinguishes between pairs of non-isomorphic covers. Along the way, we construct hyperbolic surfaces X and Y with the same full unmarked length spectrum but so that for each k, the set of lengths associated to curves with at most k self-intersections differ.