We address the macroscopic quantumness of the state of mechanical systems subjected to conditional protocols devised for state engineering in cavity optomechanics. We use a measure of macroscopicity based on phase-space methods. We cover the transition regime into strong single-photon coupling, illustrating how measurements performed over the cavity field that drives the dynamics of a mechanical system are able to steer the latter toward large quantum coherent states. The effect of losses is evaluated for the case of an open cavity and analyzed in terms of the features of the Wigner functions of the state of the mechanical system. We also address the case of engineered phonon-subtracted mechanical systems, in full open-system configuration, demonstrating the existence of optimal working points for the sake of mesoscopic quantumness. Our study is relevant for and applicable to a broad range of settings, from clamped to levitated mechanical systems.