Advice on Speaker upgrade vs System Component Upgrade

Hi Audiogonners,

I'm getting a bit of an upgrade itch, and looking for some advice about which direction to go. My current system is in my profile - small room 11x11x8 but sounds pretty good. Dynaudio Heritage Specials with DIY Aleph 60s i just built (fun!) - nice warm mid range / bass which i've enjoyed (mostly speakers),  also have a Parasound JC5+ which is nice too. I'm tempted by some of the following speakers but not sure on room size being a challenge for full sized towers. 

I listen to a lot of Pink Floyd, Led Zeppelin, Bowie - classic vinyl, but mostly on the roon rather than my turntable as my vinyl collection is really small. I love the sound of both digital and vinyl - but my digital is pretty warm with the R2R and the 

Looking at stepping up to speakers in the 10-20k range new but buying second hand;

Wilson Audio Sabrina's - $10K ish on Audiogon

Sonos Faber Olympica Nova ii - $7K used at local dealer

Or would i get a better result upgrading something like the DAC or Streamer. I'm just a bit unsure. And yes I know that the two speakers are very different sound character with the Wilsons being super revealing and probably very hard to set up in my small room. I have Kef R11s in the living room with the JC5, which are much more neutral than the Dynaudios, but they also sound great. 

Anyway - just looking for some perspectives - I'd like to move up a level with detail / clarity while still keeping that musical mid range..

Thanks in advance