Hi Peter.
(It was only a question of time!)
Overkill isn't necessarily a bad thing if it has a positive effect, even though the effort seems unproportional. In the case of the Hugo (TT) that's questionable in my book (and
Rob Watts', the
developer's). That said, «good» sound is always a personal thing. There's nothing wrong with a GS-X Mk2 in the signal path if you like this specific sonic characteristic more than anything else. But keep in mind that in this case «overkill» comprises a signal degradation by a redundant amplification stage. Since there's no way to bypass the Hugo's internal «amp», any additional amp will add distortion and signal rounding, no matter how «good» it is: it will never be as good as a piece of wire. In fact every single electronics component colors the sound, let alone a whole amplifier. Add to this that the Hugo (TT) has exceptionally low harmonic distortion (according to the specs and the developer), so any additional amp will most likely increase harmonic distortion by a considerable degree.
However, signal accuracy per se isn't the main concern in audio – the most important thing is the end result, the sound of the whole chain. Although sonic preferences vary to a wide degree, I believe you that the HD 800 sounds better with the detour via GX-X Mk2. If it's due to warmth added by the additional distortion or due to a slight shift of sonic balance provided by the amp's transient rounding, hard to tell. In any event there seems to be some synergy effect going on. But technically speaking you're sacrificing transparency. Now I'm all for tayloring the sound to my own sonic preferences, but I'm trying to leave the signal as pure as possible by doing so. And even if added distortion will sound more pleasing to the ears at fist glance, I will always refuse to go this route, as tempting as it may be. So for creating optimal sonic balance with a given headphone if the signal at hand doesn't provide it (which is extremely unlikely) I use an equalizer. I guess you haven't tried that yet. Of course it won't provide the same sonic result, but who knows, maybe an even better one – minus some spectacular traits an amp is absolutely capable of adding.
Still there's some aspects that may speak for an additional amp nonetheless, but they're hard to quantify. One thing is balanced drive. So far nobody has been able to plausibly explain the technical merits of it, but I'm open to it. Another thing is power supply. A really powerful and quick power supply could indeed help with the reproduction of dynamics – as the TT itself seems to prove in comparison to the normal Hugo. But from what I get the effect is the same for both DAC and headphone amp use. However, I can't imagine that these two aspects can outweigh the obvious signal degradation they have to accept – if they're relevant at all.
It would be interesting to hear what Rob Watts has to say about the latter aspect(s).