The only times I have ever used the standard toslink optical out of anything, I have preferred the coax (and that's a fair number of times, on both decent and far from decent digital sources). Both times I have heard a toslink vs USB implementation out to a DAC (not a huge sample but you takes whatcha got), the USB has been a no-brainer. From everything I have read, the culprit is the toslink optical interface which is jitter-prone. The USB interface is in many cases prone to power supply interruptions. I expect that it is probably a "pick-your-poison" kind of situation unless you can adequately isolate things.
I have not tried it, and have no affiliation, but if your DAC has a coax (S/PDIF) INPUT, you might try the Hagtech USB-to-SPDIF-converter. You could use your iMac USB out to this device, and from there into your DAC. Wouldn't need an AppleTV, though that would require using the iMac as your "interface," and the AppleTV is quite a bit sexier as a box (though does that mean if you use AppleTV and not the iMac that you have to use your TV when you want to choose your music?)
I have not tried it, and have no affiliation, but if your DAC has a coax (S/PDIF) INPUT, you might try the Hagtech USB-to-SPDIF-converter. You could use your iMac USB out to this device, and from there into your DAC. Wouldn't need an AppleTV, though that would require using the iMac as your "interface," and the AppleTV is quite a bit sexier as a box (though does that mean if you use AppleTV and not the iMac that you have to use your TV when you want to choose your music?)