Advice on Speaker upgrade vs System Component Upgrade

I see your dilemma. Looking at your equipment I have to say it is pretty well balanced. No obvious one piece that is really weak compared to the others.

You have excellent speakers, and so are the Wilson and Sonus Faber. But they definitely have a different character. The Wilson is going to be more detailed and descrete image oriented and the Sonus Faber more musical… with great detail… but a bit less in your face (like real acoustic music in real life is). I would think the Wilson is what you are specifically asking for. I am not aware of how old the Wilson’s are. You should probably listen to them and see if the draw to the Wilson is what you want. The Wilson will have much greater presence and authority.

Now, if you make that move… assuming you are putting yourself into a $15K - $20K newish area, then over time you would want to upgrade the rest of your equipment to get the most out of you speakers. So, if you do lots of research and find the best possible gear that has the electronic character you want then you should double your investment in each (or more) and each new component should give you a “wow”. So, thinking $5K per… Streamer, DAC, Preamp, and amp. That system should be at the next level if you have done everything right and will be a hugely better system.

Thanks for the great advice @kota1 ​​@ghdprentice - really smart stuff

@kota1 I have looked at room treatment but for my small listening room/office , i don't really play loud at all ~ 80-85 DB, and often late at night, and haven't noticed any overpowering bass so far. I do close the curtains which were bought as they are a little heavier for sound absorption to avoid the window problems. I did read recently that getting some treatment behind the listening position is maybe the most important for preserving imaging & soundstage - I think i could definitely start there and hang some blankets and see if its a big impact. 

@ghdprentice - what a beautiful system you have - and a wonderful room to listen in - its certainly something to aim for!

I have been in a dilemma with the living situation - the living room is 25*60*8ft, and I have the Kef R11's there in a home theatre setup, but i do most of my listening late night in my office, so i'm trying to figure out if i can get the next level speakers to work there and get my use out of them, or be forced to the living room where i might not get the same amount of use. I'll figure it out. 

Makes perfect sense that if i decide to the 15-20k level on speakers i'll need to replace the other components overtime - as and when budget permits. But in the shorter  term i can get the speakers and i think my components are "good enough" to get a lot out of whatever speakers i get next even if its not the max. 

I'm leaning Sonus Faber though, because they have the musical mid range and more of the Dynaudios, and they may have more detail - They have better WAF too, so if i move them to the living room at some point, that might actually be a positive from my better half, and finally - I feel like the Wilson's need a really great room to work and would be very hard to get the most out of in my small office. 

Lol, #firstworldproblems!

Thanks - much food for thought

You will get much more bang for your buck upgrading your speakers. The Sonus Fabers are a better value and you have the amp to drive them.

Your local dealer would probably deliver and set up the speakers in your home for you to evaluate for a time, especially at that price point.  I’d have a console with them to see what they think. 

A few thoughts…

First, that’s a tough room not only because it’s small but because it’s square — it’s a bass nightmare, and I would not try to shoehorn floorstanders in there because you’ll have to fight those issues and may not even be able to overcome it.  Before I got a house I had an apartment with a 13x13 living room and it was a disaster for bass issues.  Don’t do it.  
Next, if you’re not already, doing it, use the i2S connection from the Iris to your DAC.  I did this and it was transformative in terms of a lower noise floor, clarity, detail, and soundstage/imaging.  Everything just popped more within a clear 3D stage.  I got these results using this cheap $6 HDMI cable from Monoprice — I’m of the opinion the HDMI cable might not be that important as long as it’s as short as possible and preferably less than one foot (I got the 0.5 foot length).

https://www.monoprice.com/product?p_id=13578

As mentioned above, bass traps in that room could improve things significantly.  Also, adding a couple small subs with room integration software like the SVS SB1000 Pro subs ($1150/pr with risk-free trial period including shipping both ways) might well be worth a try rather than struggling to wrestle floorstanders in there.  You’ll get the full-range experience, but the bass will be much more flexible and manageable, especially in your room.

On the more extreme side you could try speakers like these nice Joseph Audio Pulsar 2s that may be a bit more transparent and neutral. 
https://www.usaudiomart.com/details/649977097-joseph-audio-pulsar-speakers-upgraded-to-pulsar-2-graphene-spec-in-late-22/

Last, if you’re looking for more detail/clarity the Aleph 60 may not be helping as it’s more on the warm/smooth side.  Have you tried the JC5 in that room?

Anyway, sorry for the brain dump but hope it at least gives you some things to chew on and hope it helps.  Best of luck in your quest!