Advice on Speaker upgrade vs System Component Upgrade

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!

Thanks all! 

@mijostyn & @paradisecom - I think its a great point about the dealer - not sure they would do an in home setup/trial on the Sonus Fabers as they are used/demo, but worth asking for sure. The Wilsons would have to be a purchase and hope through audiogon as i'm not quite ready to pay full retail & get the in home trial.. maybe - we will see - bonus season is coming...

@soix I do have the i2s - its the reason i got the iris - i have a nice Tubulus concentus cable, and i definitely noticed the difference right away. my system is very quiet. 

I have a single Kef KC62 and it's nice and doesn't overpower - but again, i'm not cranking out real high listening levels normally, so i haven't felt the need to manage bass and do treatments... but if i do get the volume up a bit, the treble on the dynaudios gets shrill and the bass gets sloppy for sure - so running into the issues. 

Funny about the JC5 - it sounds good, but tighter - I was really wanting to try out the Pass labs sound and ended up deciding to build the Aleph 60 monoblocks myself for fun, and also i wasn't ready to buy an amp (XA60) for what i'm planning on spending on speakers. If you are interested - check out DIY Audio, and i can give you the name of the guy who sold me the circuit boards and mosfets on etsy - awesome guy Randy who really held my hand - great learning experience, and i got to taste the Pass sound - more holographic and smoother for sure - a little softer, but sounds really nice for what I listen to. I also built the simpler Amp Camp Amp which is even more holographic (2nd order stuff) but its too low power for my Dynaudios and Kefs for sure. Anyway... thanks for the suggestions....

But really i do love my system as is - I've just been wandering through roon  this afternoon, and it really is a good system - it sounds great for my listening room and levels/late night listening and I think that is the answer... if i'm going for that next level its going to have to be in the living room where i'm not fighting the room so much - i can replace the Kef R11's with Sonus Faber / Wilsons.

Interesting you mention the Joseph Audio pulsars - the dealer has some JA RM33SI's used .. but not likely that real next step up but might be fun.

So many possibilities.. i kinda hate the upgraditis but its also the fun part right lol

Oscar Trio - Marten ... low order crossover / bass / build quality.

From Mfg website: 

• Copper foil air core coils
• Silver/Gold capacitors
• Supreme resistors
• Jorma internal cabling 

Bases covered.

$11k msrp

https://parttimeaudiophile.com/2021/02/14/marten-oscar-trio-loudspeaker-review/

My recommendation is to listen to martens or similar.

I'd keep the HS in the office and upgrade the KEFs to the Olympica's.  They are absolutely gorgeous, I might change out my OG Contours with the Sonettas in my home theater just based on looks. 

The HS is a near perfect bookshelf, I don't think either the Sabrina or Olympica will be an upgrade, and as soix mentioned could lead to bass issues in a small room. I heard the Tune Tot and Nova I so it was bookshelf vs bookshelf.  HS was the best to my ears though that Nova was pretty and the Tune Tot was a cool red color.  Not my taste but they looked expensive.  And were.  

If you are going to spend money looking for a meaningful upgrade then the only choice would be speakers. As far as asking which one to buy you will need to rely on your ears over opinions.

You can add all the fancy cables you want. You can upgrade your amplifier/preamp or receiver. Buy a new CD player or streamer or whatever, it will not erase the sound  of your old speakers. Might hear very, very small difference.
 

Nothing compares to a significant upgrade in speakers.