Try troubleshooting to see if the rips were bad by playing directly from the cd. Also make sure you're not running a bunch of apps while ripping. Welcome to the Mac camp.
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I assume you're using the toslink optical output on the iMac? Check to be sure you're actually importing the songs using the codec you've selected (apple lossless). Maybe something as simple as dirty CD's?
I have a 2005 Powerbook G4 and playing Apple Lossless (or even 256k / 320k MP3's) across wireless to my Airport Express, (which is attached using toslink optical to my DAC) sounds marvelous! My ears can't tell the difference between that and playing the actual CD.
FWIW My DAC is the Stello DA-100, CD Player is a Theta Miles, Amp is a Cary SLI-80 and speakers are Taylo Reference from Tyler Acoustics.
I don't think it's the way the files were ripped....I enabled the Mac sound output and played via the Mac soundcard to my speakers and I hear none of the trash- it actually sounds okay.
It's only when I set sound preferences to USB Audio, plug the USB Dac in and listen through the USB Dac/Headphone combo that it sounds bad.
But that same Dac headphone combo on my windows rig- using ASIO4all and J. River media player- sounds pretty good.
So it must be the way I have the Mac audio setup, or the 16 bit Dac in the Glow Audio Amp 1 is somehow incompatible with the output from the Mac?
Please keep the help coming!
i have multiple macs and have not had the issue that you are experiencing. i am assuming that you are using a usb cable. try a different cable. also, i used to use a usb setup and switched to using the mini to toslink with better success. it allows me to use more audio devices (jitter reduction devices, audiophile type dacs with toslink,coax,aes inputs) and the cable sounds much better. welcome to the MAC world. you will be glad you switched.
Maybe the plug-and-play USB interface chip that they used in the USB DAC is at fault. If it does not support 24/96, this is usually the clue. A better quality USB interface and associated clocking will improve this.
Have you checked the utilities-MIDI settings to make sure it is set to the correct sample-rate? Mac's usually default to 24/96 and it can use the wrong upsampler. Close iTunes and then go change the sample-rate and then re-open itunes and try again.
Make sure you turn off Sound Enhancer and Soundcheck in the option. It can cause wrong volume level and clipping.
If you are hearing dropouts the problem must lie in hardware somewhere. Since both your iMac and DAC are new, either could be the culprit.
I had a similar setup, using Macbook Pro and Dared tubed USB DAC + headphone amp, very similar to your glow audio. I really enjoyed the sound. Never had any problem with that setup.