What direction with new DAC?

With any new or cutting edge technology you are always best off waiting as long as you can to jump aboard in that new technologies continue to improve and mature over time and with successful ones prices tend to go down as well.

"With the almost daily changes in computer audio, when do you jump in for an upgrade?"

Good question.

The easy answer is whenever you think you need one.

DACs in general have continued to improve and the cost for excellent performance gone down in recent years as well.

I have two SS DACS in my good systems currently, one, in my big, main system is an mhdt Constantine that is several years old. The other is built into the Bel Canto C5i integrated, which is newer and a current model in teh BC line, that I use in my smaller system. I use similar OHM speakers in each but the sound of each is much different for other reasons. Most likely the different DACs used and and ARC tube pre-amp I use in the larger system. But both are very musical and I can sit and listen for hours. I suspect I could do better than the older Constantine in terms of detail and resolution I hear in the newer DAC. But I won't know until I decide to try something newer and different. But I also tend to believe if it ain't broke, don't fix it. I have yet to give DSD specifically a second thought.

"Mapman, isn't this whole hobby built on want instead of need?"

True. But if one truly loves music, or anything for that matter I think there is what might be called an inherent need to be able to get the most you can out of the time you invest, without breaking the bank in the process of course. YMMV in terms of what exactly that entails.