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If you have a MAC, you don't need a DAC
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Audio gear is never really about needs, right? 😉 (unless it's your job)
Definitely your first headphone upgrade will be the biggest improvement to sound quality. Whether or not subsequent upgrades yield meaningful changes is subjective.
If you haven't, I would encourage you to try out dedicated DACs and amps. Might be surprised by what you hear (or don't hear).