Do you belong more to souce first or to speakers first school of thought ?

@mitch2 this is a reasonable way to look at the source versus speakers question.  In my main system, I shopped very carefully for the amp and speakers that met specific criteria I had for my room for both two and multiple channel uses (macro).  I have not felt a strong desire to replace those and have focused instead on improving sources and tweaking cables (micro).  Improving sources in this system have allowed me to get the most enjoyment out of my “macro” gear, and finally cure the upgrade bug.   

In my office system I have more modest amplification and speakers, but did not get the full benefits of what they had to offer until I placed a proper DAC in the chain.  In both cases, my systems were source limited, crap in, crap out.

One last comment, the performance envelope of budget speakers and DACs have improved significantly over the last decade.  If you can live with more pedestrian looks, you can get pretty high audio enjoyment for modest outlays of cash these days.  Achieving the last 10-20% of performance requires significantly greater investment, and probably should start with the listening room and power supply.

kn

Speakers and amps start to get very competent around 7-10k. You can triple that price and only get a different flavor of sound.

My advice is now find a speaker with a sound you like, then go to the moon on the source. Not just the DAC, but grounding, power distribution, streamer, equipment isolation, cables, e.t.c, can reveal a sound that you never thought possible from your speakers.

If you just had a normal equipment chain, good speakers can be ALMOST there, but there is always something unsatisfying. So you end up on the speaker merry go round (and amplifier merry go round). When you ignore the dac/grounding/power/cables chain, you never really heard what those speakers (or amp) were capable of.

I can now see this is the situation most audiophiles are in, including myself until about 10 years ago.

Also it doesn’t matter if your source ends up being multiples in price of your speakers. You don’t have to buy a top line speaker to match, as often the top speaker model has a half dozen drivers and is designed for a cavernous listening space and requires very high wattage amps, which if not setup carefully can reduce it's performance to below that of the middle tier models (which are much cheaper).

@agisthos +1 both posts.  I would add room design/treatments to your list as well, maybe first on the list.

Speakers only matter up to a certain price point if you understand room acoustics, setup and the art of integrating subs.

Thereafter, all the flagship nuance, high end magic, etc is created by the front end electronics.