In spite of significant recent and ongoing research efforts, most of the early evolution and long-term fate of young massive star clusters remain clouded in uncertainties. Here, I discuss our understanding of the initial conditions of star cluster formation and the importance of initial substructure for the subsequent dynamical-evolution and mass-segregation timescales. I also assess our current understanding of the (initial) binary fraction in star clusters and the shape of the stellar initial mass function at the low-mass end in the low-metallicity environment of the Large Magellanic Cloud. Finally, I question the validity of our assumptions leading to dynamical cluster mass estimates. I conclude that it seems imperative that observers, modellers and theorists combine efforts and exchange ideas and data freely for the field to make a major leap forward.