What would you upgrade?

I would start with the Emotiva amp. Not sure if the Dared is a preamp, but if so, that would be next on the list for me.

Shakey

I would put it all into a high quality integrated amp.

My suggestion is to update/upgrade your DAC with the latest Asynchronous USB input for your Mac. $299 for Parasound ZDac or $5999 for the newest PS Audio Directstream.

"Clearly a lot of room for improvement here."

Ummm...how exactly is that? That's nice equipment - you didn't get any of that by buying 10 gallons of premium unleaded at 7-11. What exactly is wrong with the sound currently coming out? Or is it just that you have $5K that is going nuclear in your pocket and you're absolutely positive that the grass must be greener?

I'm being serious, not sarcastic. Sure, you can definitely have nicer, more expensive equipment, but the OP has zero detail about the room all of that equipment is in, the kind of music being played on it, the quality of files being played, or how it sounds now. Seems like it's spending $5K just to spend $5K. Which is fine too - if that's the case, let us know - lots of cool ways to blow $5K in audio!

I have a Decco 65 in my office setup. It's a great piece of kit for the price. The onboard dac in the Peachtree is on a similar plane as the DacMagic. For the sake of simplicity and $$$ I'd personally go mac into the decco and put your money into new speakers you've listened to and love. If you want to move up a notch check out Peachtree's Grand X1 or a Naim SuperUniti.