Should I upgrade DAC, speaker cables, ICs, or PCs?

Never upgrade a cable when you can make a legitimate component upgrade.

I've owned the Havana, Benchmark, and DAC3... you can do better for the money.

OK Mintzar, looks like you want to be asked: what are your suggestions for doing better than those components, for the money?

The Zardoz Ultimo Transport starts around $1k and goes up to around $4k depending on the upgrades you want. It's a superb DAC and will also allow you to send music wirelessly from your Mac Mini (cuts off the source, feel free to message me if you don't understand how network transfer works).

The Other option is the Mojo Audio DAC, which I've been somewhat beta testing over the last 6 months. It's better than the Z, but it'll cost right around $2k.

There are other options in the pro-audio realm, the TC Studio Konnect 48 is a stellar piece of gear for $700-1k. If you aren't familiar with routing and using pro-audio I can help with that. But the TC is lower noise than the Mojo Audio and Z. We can get a little more expensive also into the $4k range and skyrocket into the $30k+ performance range.

Of the three units you mentioned the Havana is by far the most musical. The problem is that the tubes are noisy. The Benchmark is VERY bright and analytical. You don't want any oversampling DACs. They destroy the emotional content of the music and give an artificial sense of detail. Oversampling uses an algorithm to correct for information that either isn't there. That algorithm creates jitter, which means timing errors. So you may have a more detailed sound, but you loose the proper time tune and tone of the music.

So I'd recommend going with a good NOS DAC. All of the DACs I mentioned I have owned or had in my system for a good length of time. I currently own the Prism Sound Orpheus.

You can't go wrong with any of the DACs I mentioned. They are all in the top tier of performance.

I've owned all three of those DAC's, and many more, and I don't agree that they would be a bad match. Everyone is always trying to get the best sound from their system and that means balance.

My system tends to bright, so I didn't like the sound of the Benchmark in my system at all, or the Bel Canto after a while. Both were excellent DAC's but too bright for the rest of my gear. In other, warmer biased systems I have heard them, at stores and audio shows, they have been absolutely stellar.

I loved the Havana on the other hand. It was warm, and with the right tube in it, silky smooth and a great value. But it didn't have the last word in detail, so I kept searching. I eventually bought a Bryston BDA-1, which to me have been tremendous. Hard to find used, and a bit out of your current range, but it really has a complete warm yet extended, and detailed sound to me. I love it. I had a Berkeley Alpha DAC that may have been a bit better, but it was more than twice the $$, so I got the Bryston and no complaints.

I guess from looking at your gear, it has a very nice, powerful and warm tint to it. A Bel Canto, or Benchmark could match really well with that set up. The Havana might sound too syrupy in that signal path. But that's just my guess, since I haven't heard your set up. But I love all the gear.

I due use the oversampling on the Bryston, it just sounds better. Also, as far as DAC's go, the newer chipsets, jitter control, and power supply advancments are the reasons I don't think NOS DAC's are in the same league as current designs. It's literally like comparing a first Generation Mac computer with a current iMac and saying the original is better.