At what level IEM wise is it worth up grading from a iFi Micro iDSD to say a Chord Hugo 2?..also maybe in the future Headphone wise would a Hugo 2 do mid level headphones justice such as Clear’s, TH900 or Ayra’s etc?..just wonder where the Hugo 2 stands?
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It really depends on the iem, when you get to the 1.5-2k point for iems, you really do want to have the amp and dac to do them justice. Of course there are other options than the hugo 2, but I do think you want to be in that range of performance for sure. For the headphone question, I do think the h2 would work well with the clear and the th900, the arya might want a tad more power but it’s actually still pretty solid pairing
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Thanks MON for that honest appraisal, kinda what I thought tbh…planing my audio/wallet rabbit hole is “falling” in to place lol.
Headphones for me take second place so at the mo 
is best spent on IEM’s 