Unfortunately, it's going to be a little hard to answer all your questions as I doubt there many people that have heard a D2 with your listed dac options versus an X1.
Will the X1 eventually become obsolete, sure....but so will every other streamer that's out there currently. Even at 5+ years of age, the X1 is still one of the best streamers on the market (Imho). We really are not seeing a ton of new streaming features in the near future that would lead to short term obsolescence.
I personally lean towards one-box streamers as my preference, but if you really would like to have a separate dac, you may actually want to consider swapping your D2 for a U2/U2 Mini in combo with one of the dacs you are considering.