Two new observational windows have been opened to strong gravitational physics: gravitational waves, and very long baseline interferometry. This suggests observational searches for new phenomena in this regime, and in particular for those necessary to make black hole evolution consistent with quantum mechanics. We describe possible features of compact quantum objects that replace classical black holes in a consistent quantum theory, and approaches to observational tests for these using gravitational waves. This is an example of a more general problem of finding consistent descriptions of deviations from general relativity, which can be tested via gravitational wave detection. Simple models for compact modifications to classical black holes are described via an effective stress tensor, possibly with an effective equation of state. A general discussion is given of possible observational signatures, and of their dependence on properties of the colliding objects. The possibility that departures from classical behavior are restricted to the near-horizon regime raises the question of whether these will be obscured in gravitational wave signals, due to their mutual interaction in a binary coalescence being deep in the mutual gravitational well. Numerical simulation with such simple models will be useful to clarify the sensitivity of gravitational wave observation to such highly compact departures from classical black holes.
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