Old days & steamers vs newer stuff?

Given that there are a ton of variables depending on speakers and other equipment. What are the generalities in comparing? something like...

1) an old blusound node 2i with an ayre codex dac

2) lumin d2 for dac & streamer

3) node 2i with giselli labs dac

Basically,  I'm asking if you think expensive old dac and streamers (lumen, node, ayre codex) still beat out the newer cheaper stuff like denafrips ares, gishelli labs, etc.

I want to improve my setup, but I'm not sure if used older higher end stuff is better than newer mid end stuff.

Quality improvements over time can often yield a newer less expensive product that is superior to older high end items.

Whatcha think in this regard when it comes to dacs and streamers?

Newest tech one can afford, or highest end used stuff one can find?