Discrete multitone (DMT) modulation, thanks to its water-filling nature, is proposed to enable flexibility in passive optical networks (PON) optimizing the PON resource usage. The exploitation of DMT signals to directly modulate long-wavelength vertical cavity surface emitting lasers (VCSELs) can provide energy-efficient transmitters for 50G PONs. At first, we present preliminary experimental measures employing both single sideband and dual sideband DMT modulation with already available short-cavity VCSELs operating in the third window to study the PON performance as a function of the accumulated chromatic dispersion and of the received power. The experimental results are further compared with simulations, demonstrating the effectiveness of the developed simulation tool. Then we study the performance of DMT-modulated transmitters based on next-generation short cavity VCSELs with higher bandwidth (up to 20 GHz), operating in the O band evaluating their chromatic dispersion resilience. Finally, considering the statistics of a commercially deployed PON, we demonstrate that DMT modulation, providing link adaptation, offers a significant increase of the total aggregated capacity with respect to single-carrier based fixedrate PON, optimizing the PON resource usage with respect to the available power budget and the dispersion impairments.