@21qz I love my iDSD Pro, but I have recently been reading a lot about Chord DAC's and I really want to hear the TT2. I would take the iDSD all day over the hugo and hugo 2, but I would probably take the TT2 over the iDSD if I could afford it. I am tempted to buy one just to hear the difference in sound quality. But I also have the iCAN Pro and the iDSD and iCAN pair incredibly well together and the shear volume of sound combinations with them is almost impossible to try them all. The iDSD by itself has 45 possible combos and when you add the iCAN that number goes a lot higher. So either way that would be a very difficult decision for me.
I wish I had a hifi store I could go to and try these things. Alas I do not and have had to purchase everything I have wanted to try. In the early stages of this hobby thats not to big a deal as you can get stuff on amazon and return it if you hate it but as you get to the higher end you gotta go with reputable dealers and those decisions become much harder.
But in all honesty I imagine you would be very happy with either of those DAC's.