Does an upgrade make sense?

In general, it looks like your system is fairly well balanced. But the streamer / DAC seems likely to be holding the rest of your equipment back a bit. @soix brings up one good possibility.

One of the great things about high end audio, is there is no limit to improvement. Typically I get to a level I am happy with and enjoy until the bug strikes, and then I slowly upgrade to the next level. Sounds like you may be there.

Typically the sequence is speakers, preamp, amp, sources. If you do this… do lots of auditioning before purchase. Invest no less than 2x.

But if I were you, I think you can get lots more out of what you have by upgrading your streamer and DAC to the next level first. This could bring you a good boost and enjoyment before rolling up your sleeves and upgrading the rest. You would enjoy more dynamics, detail, impact. I would recommend looking for a separate streamer and DAC.

To get a feel for what to invest, I would look at the cost of your amps and preamp and plan to spend about 2x what the average cost of those functions. So, if they were around $2K, then look to invest $4K in a DAC… then $4K in a streamer.

This sets you up to later do the speakers… which should be done with lots of research, as changing those will likely change the sound of your system significantly. Lots of auditioning before purchase.

I can't tell from looking at your system's photos, but you might want to re-address your set up to make sure you have optimized your system's potential. It looks like your speakers are on the 'long wall' and it looks like your speakers are a bit closer to the wall behind them. If possible in your room, set up on the short wall firing down the length of the room will give you a fuller sound, more pleasing to most folks. As presently set up now another foot out from the wall could give you a bit more sense of 'air' and depth (you have to adjust your listening chair as well). 

But if all that is moot, and you decide to go with some subs, consider whether or not you will use the subs with a crossover, or if you will drive your mains full range with the subs just additive in the lowest range. FWIW I hate crossovers.

Thanks all. Good ideas to chew on. The speakers are actually out further from the wall than in the pics.  About 30 inches from the rear of the cabinet to the wall. The room is a huge finished basement, roughly 36’ square. So there really is no short wall available. My lil oration is I can’t move my chair back any further so the speakers can’t come out any further.  But I’ll think about a total redo of the room. 

Subs are a good suggestion too. I’ve had a single sub in the past when using an AVR as a preamp. I don’t feel a lack of bass but I understand what they can do to free up my speakers.  But I don’t like crossovers either. 

in terms of streamer and DAC, if I were to go separated, DAC first?
 

Yes. I would go DAC first. That is going to have a bigger impact on the tonal balance. The streamer on level of detail and noise level. Of course they are interrelated. But DAC definitely.

+1 for DAC first.  Then Roon ... I love it and it takes your streaming experience and music discovery to a whole other level.