Since our first discovery in 2015, gravitational-wave and multi-messenger observations yielded a number of "surprises." We have detected more and heavier black holes than anticipated; multi-messenger emission from neutron star merger GW170817 showed structured high-energy outflow and produced a multi-component kilonova; and as recently as last month, we announced the discovery of a curious object found in the so-called mass gap, while an optical transient was associated with a very heavy black hole merger. In the next five years, LIGO's expected detection rate is set to increase twentyfold, to one event per ~hour, promising many more surprises and new questions we can address about source populations. I will review several of the new interesting directions in gravitational-wave and multi-messenger observations that began only recently and promise to substantially enrich this field in the next five years.