The answer isn't one or the other. It's too dependent on how the connection between the two is implemented. A cheap transport and a cheap DAC with a well implemented I²S connection may sound better than their expensive counterparts with a optical TOSLINK connector.
In direct answer to the poster's equipment choices -- I think you're more likely to get better sound with a new CD player.
In direct answer to the poster's equipment choices -- I think you're more likely to get better sound with a new CD player.