Advice on System Synergy

I am slowly putting together a system and could use some advice on system synergy. Some of my favorite music isn't recorded all that well, so i'm aiming for a system that won't make these albums totally unlistenable.

My Source is a macmini playing lossless files, and speakers are Devore Fidelity Nines. I have up to $5k to spend on a DAC and amplification.

Given the above, would welcome opinions on whether the following Would be a good match:

DACs: either the Benchmark Dac2 hgc or the Woo Wa7, primarily because of their preamp capabilities.

Amplification: Bel canto ref500m
Thoughts, or Other suggestions?
Can you give an example of some of the recordings? Also, what kind of music is it?
I get it.. Dac's I'd look at the Ayre QB9DSD, Wyrd4Sound DAC2se DSD, or maybe a PS Audio PWD MKII

Amps I'd look at maybe a Plinius 9200, BAT VK-300x se, ARC VSI60, Primare I32

First, I would recommend to power the mini from an external Linear supply, preferably a SR5 or SR7. This will make a huge difference in dynamics.

Second. I would recommend to use Amarra symphony for player.

Third, get the "audio optimization guide" from iTunes iBooks and do these tweaks to the Mini.

Third, replace the HDD with a SSD for the OS to run from. See for details:

Fourth, try all of the USB ports on the Mini to find the best one. I know which is the best on 2009 Mini.

Fifth, make sure you are ripping CDs using XLD with Accurate Rip enabled. Much better than iTunes:

Finally, if you are in the $5K price-range for a DAC, consider the Overdrive SE, just reviewed by It came out on top when compared to other DACs, like Bricasti and Analog DAC etc.. You will need dCS Vivaldi to come close IME. There were Vivaldis in rooms on either side of my room at the last RMAF and I'll take the Overdrive:

Steve N.
Empirical Audio
Steve, I read the audio stream review and don't understand your statement "It came out on top when compared to other DACs, like Bricasti and Analog DAC etc."

Here is the paragraph comparing M1 vs Overdrive SE:
"The Overdrive SE sounded closer to the tonal balance and general sound of the Bricasti Design M1 DAC. The $8995 Bricasti was even faster and more resolving in the midrange and highs than the Overdrive SE and while possessing much of the general ease of the Analog DAC. Adding the Final Drive, Short Block, and direct balanced connection brought the Overdrive SE’s performance closer to that of the Bricasti Design M1."

Am I missing something?