Help: Order of importance: Pre, Amp, DAC, speakers

This is very subjective, however my vote goes to the preamp being the most important. The reason I would put electronics ahead of loudspeakes is that, though loudspeakers change the sound to a greater degree, that change is often euphonic and consonant with the music itself. Electronics produce, well electronic distortions that are not consonant with the fabric of the music and are much more annoying, even in small amounts - to ME. Additionally, the preamp deals with the lowest level signals in the reproduction chain, other than the phono preamp, routes them and switches them; a lot gets messed up in the preamp. Finally, my order: preamp, amp, DAC, loudspeaker. Of course room treatment, power management and cables belong in there somewhere.

Speakers far and away.

Does the Pre, amp and DAC really shine above a speaker purchase?

The system can only shine as much as the speaker will allow but good electronics is a great start.

Both the speakers you tried are very similar in size and design and purpose (near-field monitors with low levels of distortion). I'd give Dynaudios the edge - they should sound smoother and more natural (btw: they are a much more expensive speaker so they ought to sound better).

To get a signficant upgrade in speaker sound you may have to consider much larger speakers without bass assistance from a reflex port (a large three way for example). This will give you a cleaner transient response in the bass and greater dynamic range without compression/distortion.

Speakers
Pre
DAC
AMP