Personally, I think the comparison in quality goes something like this:
SkeletonDAC < grubDAC << pupDAC. I believe the designer of all three - cobaltmute - feels this way, too. We go to great lengths to try to match up cost with proportional quality at Beezar.
The pupDAC has an opamp for its output, so it will do much better driving a headphone directly than the other two. Keep in mind that it's still USB power, so the voltage and current will be limited. For an incredible treat, though, try listening with some quality IEM's directly from its output.
The SkeletonDAC has a headphone amp built into the newest PCM2704/5 chips, so it will do well, too. The problem is that the SkeletonDAC depends on filtering capacitors at the output and you will lose bass with low-impedance phones unless you make the output capacitors large enough. This has to do with the bass-filtering effect of the RC circuit formed by the headphones's impedance and the output capacitors' capacitance. An RC circuit has a calculable cutoff frequency at the low end. Since you can't easily change the headphones's impedance, you need to upsize the caps. I have powered KSC-75's using 47uf, 6.3V capacitors on the output of a SkeletonDAC for extended periods. It sounds pretty good, although the bass sounds a bit artificially tight, probably due to some artificial filtering in the lower frequencies.
The grubDAC has neither an output opamp nor does the Wolfson DAC have a built-in headphone amplifier. IMHO, it will probably do the worst with a direct headphone connection.
As Avro_Arrow points out, all three DACs are really designed to be sources, not drivers of headphones.