Yes, the headphone out of the Macs doubles as a mini-jack to optical toslink output. This then goes into the optical connection of a DAC. You can also use a USB to s/pdif converter for the coaxial input or just USB, but it depends on the inputs the DAC has and whether they have all been made to the same quality. They'll all pass the bit-perfect test but if you move your mouse and hear it create noise through your speakers when using a USB connection...
As said, the actual DAC chip used isn't as important as how it's implemented, a DAC is primarily an analogue device, which is why you can see the same chip in 10 different DACs across large price ranges and they won't all sound the same. As for sound quality improvements... if you look at somewhere like Gear$lutz, who are well and truly against audiophile silliness, the majority of experienced posters will tell you that no1) however good the chips are these days, no DAC is 100% transparent and it's a case of how far you want to chase diminishing returns to get something that's as clean and true as possible, and 2) it's not worth putting down 3 figures for a Benchmark or Lavry when you haven't even got decent speakers or done anything about your room acoustics, so don't get sucked in. I'm not a massive headphone guy but in the same vein, I wouldn't even be looking at fancy DACs unless I had highly resolving headphones like the HD800s or Stax or something (and the appropriate amplification to drive them fully).