Old digital front-end vs. bleeding edge

Hi all. What are your thoughts on old faithfuls versus new front-end kit - at approx. the same cost? Specifically if you want to playback files from a computer / music server....for the new price of a modern DAC with USB input, high res and DSD support, etc. you could also consider an older unit (such as a ML DAC or an Esoteric CD player with digital input) - using a USB to digital interface.

The two concerns I'd have are support for modern hi-rez formats such as DSD, and support/maintenance/spares for older units.