As someone else stated, for $5k I would just start over and sell your current equipment. But, for an upgrade path and more conservative approach...
Since you already listen to ripped CDs (hopefully at full resolution), why upgrade the CD player? Save the money for other components. I would do the following:
(1) replace the Connect with a Bluesound Node 2i. Good server and decent DAC (and you can always add an external DAC later). $500
(2) Get an entry level power condition from Furman or Audioquest. $200 or so.This actually made a noticeable improvement in my modest, second system.
(3) Get a high-res subscription service like Tidal or Qoboz.
I would do this before anything amp or speaker related. See how they sound with an improved front end before moving from there.
Since you already listen to ripped CDs (hopefully at full resolution), why upgrade the CD player? Save the money for other components. I would do the following:
(1) replace the Connect with a Bluesound Node 2i. Good server and decent DAC (and you can always add an external DAC later). $500
(2) Get an entry level power condition from Furman or Audioquest. $200 or so.This actually made a noticeable improvement in my modest, second system.
(3) Get a high-res subscription service like Tidal or Qoboz.
I would do this before anything amp or speaker related. See how they sound with an improved front end before moving from there.