I believe that question has already been discussed. Yes, in theory the devices are not in sync with one another, but AFAIK that's not a problem. Here's why.
This topic was originally created following a private chat between sweetchaos and me. That conversation was about me wanting to have dual headphone listening sessions with my girlfriend. In that case, the fact that the DACs are not in sync doesn't really matter (at least in my case with my two E30 DACs).
With separate listeners and separate headphones, the fact that may be a small delay (probably unnoticeable anyway) between both headphones just won't affect the listening experience for any of the listeners. Even if there was a small increasing time shift between both DACs, that shift can be estimated at about a couple of samples per second (or so I've been told). For a 4-min song, that's about 480 samples. So about 0,01 second. None of the listeners would be able to tell who finished first.
Of course after 40 mins of uninterrupted music, that time shift could start to maybe become noticeable (not even sure), at about 0,1 second. But here's the trick :
every time you pause/stop/restart music, the time shift is reset. So unless you wanted to listen to a very long playlist with somebody else and without ever stopping the music a single time, that wouldn't really be a problem.
Besides, I'm not an expert, but Voicemeeter has a big audio buffer that may also be helping with this. I don't know all the technical details, I can just say that it works. I'm talking from experience. In our dual headphone listening sessions it all has been working perfectly for a year or so:
- sweetchaos' method for all the building blocks,
- Mega Switcher for setting two different EQ presets simultaneously, one for each headphone, with real-time fine-tuning.
Maybe other people will encounter issues, but we don't. We are very happy with this.