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Recommendations on a DAC/Amp combo
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A few options to consider:
AQ Dragonfly 1.2 - these are being cleared out and can be had for $70-$80 if you look around. I picked up one for my work laptop and have been quite astounded by its performance. I've ran it with various different IEM's and full-sized HP's including the T1 and it did a pretty solid job with all of them. You will need a splitter as CEntrance mentioned.
DACport Slim - I would choose this over the Dragonfly if 192/24 bit support is needed. I was eyeing it for the office role but I don't listen to much 192/24 music (at the office), I saved $20 bucks with the Dragonfly and I got free 2-day shipping. I don't have first hand experience here but have researched it thoroughly.
Schiit Modi + Magni Uber - this puts you at $250 plus shipping BUT gives you significant versatility that most other options in this class can't match. This is a separate stack so you can swap the DAC or Amp as you requirements change or the product reaches the end of its life. The Uber includes variable pre-outs that would let you control your powered speakers without adapters and extra gear. I don't own this combo but I do own other Schiit gear and have been more than satisfied with it's price to performance ration. I researched an Uber stack thoroughly as I was eyeing it for a bedside rig, went with MassDrop O2 instead. Still might pick up a DACport Slim to go along with it, using my X3ii as a source now.
If it were my money I would stretch the budget with the Schiit stack. It accomplishes all of your goals and allows plenty of room for growth. The Magni has the ability to handle a wide variety of headphone loads. I am also a bit biased as I prefer to have dedicated components over "combos" in almost all aspects of audio. I like to be able to swap out one piece of the chain without affecting the other components.