Wall circumference is a good metric to keep in mind. Via hole size determines via circumference, and I usually use larger diameter vias for nodes like power or ground that would benefit from lower impedance. The height is determined by your stackup, so you can't control that. In my boards, vias go through the entire board, and there's a necessary keepaway distance, and disruption to all layers. I feel that this keepaway requirement favors one larger via than a few smaller ones. Inductance of the via will be reduced with a larger diameter, as it will using multiple parallel vias, but I think it's more efficient area-wise to use one larger via than a few smaller vias. Finally, I have only found a few instances when more than one large-ish via was good to use, and it was mostly related to needing to keep these vias arranged in a compact line.
So, on the balance, I prefer one larger via over several smaller ones, as they seem more space efficient, and can have very low impedance if you scale them properly.