While a lot depends on the specific implementation of both the D/S and R2R DAC (and the filters), each can give you a different flavour for sure.
Some straight-off-the-spec-sheet D/S DACs in particular can be very harsh in the treble, for example. Of course, R2R dacs with inaccurate resistor ladders can sound pretty poo and indistinct in their turn. Main thing is to have a good implementation of whatever you like. I'm not sure that there's a type you "should" be using (D/S vs R2R, OS vs NOS etc.)- more that you probably should use a unit that sounds good. There's more than one way to skin a cat.
Me, I'm quite happy with my modest Gumby (it's effectively R2R, just the resistors are in-package in the DAC chip), but I'm sure there are a good few decent D/S DACs that I'd enjoy too.