How would you upgrade my entry level system?

... and I'm assuming you have fully broken in your equipment - that means 300+ hours of continuous play (I usually do double that): most never really break their equipment in, consequently never really knowing how good their equipment really is...

I like the existing sound.
would just like to more captivated, can't articulate it any better than that.

Don't need to. Captivated is perfect. Captivated happens when your senses detect something is really there. Captivated is better than fascinated. Captivated you are caught. You are drawn in. You can't, or even better don't want to, get away.

What gets you to captivated isn't in-your-face dynamics or flat frequency response or any of the normal audiophile BS. What gets you captivated is the sense of subtle inner detail lurking just beneath the surface. Kind of thing makes you want to listen closer and more intently. Deeper and deeper into the recording.

You can buy the best speakers, amps and CD players in the world and you cannot get to captivated that way. No way. Never in a million years. All you will hear doing that is your crap lamp cord, patch cords, and freebie power cords. And boy will you hear them good and boy will it be annoying.

The way to captivating is carefully auditioning at home every one of your components including all the wires until you find the ones that beautifully balance and bring out the best in all the other components. Captivating doesn't have to cost a lot of money. It costs time. And effort. But man is it worth it. 

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. 

Don't know what you're using but you might consider upgrading your power cables. 

Think of it like you're building a house. First, start with a solid foundation ie. room treatments (GIK or ASC) and vibration control (Herbies has affordable options). Next. address your incoming power ie. power cords (many options out there, buy used) and outlets ( also dedicated lines of possible). Doing these things will pay off in the long run no matter what gear you get in the future. Good listening. Jeff