Can You Beat Simple?

I am trying to upgrade my digital source, but ultimately I find that the simple solutions work best. For example, I installed a DAC with asynchronous USB and fancy upscaling technology. I added an aftermarket power supply, RCA cables and USB cable. It sounds fantastic, actually. It does almost everything better than my CD player it replaced, except for one thing: musicality. It’s very fun to listen to and you can hear details like no other, but when I try to sit and relax and just enjoy the music without over-analyzing it, my cheapo CD player (an old portable one actually) with upgraded power supply is more relaxing, musical, and most importantly, emotional. What’s going on here? Why doesn’t modern technology take the cake in this situation? Are we heading down the wrong path with all this fancy technology including upsampling, asynchronous data transfers, ultra-high bit rates, etc? Does anyone ever stop to ask the question: Can your solution best a cheap portable CD player that should have went extinct with the dinosaurs?