Best set-up under $20K

I did forget to mention in my post that system 2 is a Ps Audio Strata. 

It's pretty amazing for the cost, especially today, and I also hear the difference between cables with it.  Nice bass slam with it as well.  It does miss a little bit of staging & seduction but is hard to beat for an ALL In One and  it bested many super expensive systems at Axpona 2023 when paired with ProAc 3.8's. 

I  agree with @vthokie83 (above).  It sounds like the most immediate concern might be the lack of a dedicated, wired streamer. You should be able to get a very good streamer for well under $5K. Even a Bluesound Node, or a Holo Red (if you can get it), might be a good upgrade for less than $1K USD.  Try that and see if you aren't more satisfied with the speakers and integrated amp you already have.

Pair of used 92.5 dB sensitivity JM Lab/Focal Mezzo Utopia's and a pair of Jeff Rowland Model 12 Monoblocks(if you can find a pair!).

Speakers will be at 4 ohms Impedance and amps at 350W @ 4 ohms. 

I seriously doubt you'll be able to beat that combination. 

I use the H360 and i am keeping it.  With a room that big, I would agree that the JBL's will fill that room and then some.  But you should go listen to them first.  Nobo dy here can guess what sounds the best to you.

Given your focus on digital, I really think you need to upgrade that chain before you make any other big decisions. You are missing out on a lot using Airplay and most likely the embedded DAC as well. Start by getting a dedicated streamer, but something better than a Bluesound Node. Lot’s of fun research to be done!