Help me get the best sound under $5K in upgrades

You might want to try a 80w or more tube amp with the Maggies. Use the powered subs to offload work from the amp and a lot fewer watts are needed. For SS, the Mc seems like a decent match.

Also I am wondering how the Maggies are set up? Placement is everything with those. Some rooms could be a challenge.

The Maggies seem like a good match for your listening tastes as you describe otherwise. The trick is to get them to sing like they are capable of. The whole setup has to mesh.

I did not see anything regarding a DAC. How do you get your music from the Mac Mini to the preamp?

Tried Parasound Halo this weekend. I think this is a winner for me. I'm getting A21 & P5, replacing the Macs. For me, they have more detail without fatigue.

I recently added Dirac room correction software to my setup (mac mini -> audiophillo -> Bryston BDA-1 -> Plinius 9100 -> Wilson Duette) and for the first time in a long time, I'm very happy with the sound of my system. The sound is much more focused, instruments are better separated, and my room modes are tamed. For me, it's proven a massive upgrade. The only risk I took was spending $75 on an omnidirectional mic to do the measurements, then I downloaded the two week trial version of Dirac. It took a bit of playing around to generate the best filter, but I'm delighted with the results. I ended up buying the software, which costs around $500. I recommend giving this a try. My system is in my main living room, and room treatment is not really practical.