How would you upgrade my entry level system?

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. 

Five grand in the context of your current system is a lot more than an upgrade and in my book calls for some serious thought.

Sounds like right now you are mostly using it for playing background music. With maybe some occasionally more dedicated listening. The point of this isn’t to see how good I am at guessing games. Its to get you thinking.

Which matters more, how great it sounds sitting in one precisely defined sweet spot? Or anywhere around the room? How likely is this to change over time? Ditto the room- will you be staying put or moving?

What are your more longer term goals? You could plow the whole five grand into a classic highly regarded speaker, one so good you could spend the next however many years building an awesome system around them and still love them. Or you might be a whole lot happier to budget the whole five grand to a whole new system.

This kind of thinking it through approach is the only way I know of getting anywhere but broke. Anything else boils down to asking a bunch of random people how they would upgrade a bunch of stuff they never would have bought in the first place. Which you just did. And got a good answer anyway.