Dipolar magnon-magnon coupling has long been predicted in nano-patterned artificial spin systems. However, observation of such phenomena and related collective spin-wave signatures have until recently proved elusive or limited to low-power edge-modes which are difficult to measure experimentally. Here we describe the requisite conditions for dipolar mode-hybridisation, how it may be controlled, why it was not observed earlier and how strong coupling may occur between nanomagnet bulk-modes. We experimentally investigate four nano-patterned artificial spin system geometries: `chevron' arrays, `square', `staircase' and `brickwork' artificial spin ices. We observe significant dynamic dipolar-coupling in all systems with relative coupling strengths and avoided-crossing gaps supported by micromagnetic-simulation results. We demonstrate reconfigurable mode-hybridisation regimes in each system via microstate control, and in doing so elucidate the underlying dynamics governing dynamic dipolar-coupling with implications across reconfigurable magnonics. We demonstrate that confinement of the bulk-modes via edge effects play a critical role in dipolar hybridised-modes, and treating nanoislands as a coherently precessing macro-spins or standing spin-waves are insufficient to capture experimentally-observed coupling phenomena. Finally, we present a parameter-space search detailing how coupling strength may be tuned via nanofabrication-dimensions and material properties