Hi Spooge!
Well, depends.
Here's my random, incoherent thoughts.
First, a lot of older DAC's still sound better than a lot of modern, mass produced stuff. The older Theta Casanova for instance still shines.
However.. in the last 5 years or so DAC's have gotten really good in a surprising area older DACs are not: Redbook.
Several modern DAC's really do CD quality sound MUCH MUCH better than older DAC's did, making "high resolution" files seem much less necessary than before. Among these I include Schiit, Mytek and Berkeley.
Best of luck,
E