I haven't done an in-depth comparison of DACs on speakers, or any A/B, but I have heard a difference in DAC over multiple listening sessions at a dealer. Using the built-in DAC on the Bluesound Node 2/i was much worse than the Luxman DA-06 unit they had on hand.
On amps, definitely so. Perhaps, in some cases at least, even easier to tell differences in amps on speakers. Many speakers require much more current and/or present a more demanding load, or have idiosyncracies due to crossovers and different driver materials that make certain amps painful.
I've heard differences in most amps I've listened to at home with my Maggie 1.6QR. I also spent most of a day at a dealer using the same Aerial Acoustics 7T speakers in the same position and just switching amps. Heard differences there too (and liked a Plinius SA-103 Class A room heater the most).
My Forte IIIs really changed their character a fair bit between different amps. A SET amp made them substantially mellower, an Aegir cooler and clearer. Dual Aegir even more so. I found my Magnepan 3.7i to change a ton from amp to amp. A huge Rotel amp was pretty bad. Dual PS Audio good but smeared. Dual Sanders Sound the best of all.
Especially with solid-state HP amps, and setting aside power needs, it seems easier to achieve competency on cans. The only solid-state amp I've truly disliked was the Jot 1. Way too steely and flat.
Much easier to tell the diffs on speakers in my case. But probably depends on how good the speakers vs headphones and how well you know the sound of them. The more time spent with one vs the other likely makes it easier to hear diffs when changes happen.
With the exception of widebander and active speaker (amp directly on driver) headphone is much less complicated load - thus simple amp produces good wholesome sound.
Going deeper - planar driver (or other damped driver) with close to flat imp curve is easier still. Conventional piston transducers with high imp swing demand high requirements from amp. Integrity over large current and voltage range spanning over wide fr range.
Ahh, forgive my smartassness - now pure opinion:
modern hi end multiway speaker is the the final boss trial for an amplifier. All odds stacked against the poor thing.
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