In my experience there is no advantage to leaving the soil dry when I am trying to root a cutting. At the very beginning, if the cut end of the plant may not have healed completely, you don't want to jump the gun with the water. Otherwise I water cuttings that I am trying to root exactly like I water the plants with roots, ie. when the soil goes dry or almost dry. This is always starting with a relatively small container which would dry out fast on its own... when there is new growth on top (indicating the presence and activity of roots) then I might move the cutting to a more generous sized pot.
