what is a lazy old audiophile to do?

A DAC is gonna be your best bet here. imo

One with USB input perhaps, though not necessarily. One can go either way... out from a sound card into a receiver, or int, or preamp via analog.

From the card into a receiver or processor/controler or DAC via optical or coax cables.

Or via USB directly from the PC then into a DAC via USB cable. There are others too.

Some even bypass the conventional stand alone DAC altogether by using the Apple Airport, Squeeze box, or Transporter. These wireless units possessing DACs that feed your audio power train via analog cables.

Lots of ways. Which is best? Don't know for a fact, but I went with a conventional stand alone DAC possessing all the digital inputs + USB for greater flexibility.

Logistics say some will have to or want to, use wireless, eg., Airport/Transporter, or a laptop and USB DAC. I understand one can even use their cell phone now with some devices.

Iv'e tried all but the Airport & Transporter as I'd still have to use a laptop to view and navigate via it's larger display.

I prefer both the sound card approach into the preamp... and the USB/laptop into the DAC. Each has it's merits. The DAC in my case is the key however... IMO.

Though there are other considerations. File types. Lossless, or compressed. media players too can improve the sound. How the files are ripped and formated as well, contribute to the outcome.

Pick your own poison. Squeeze box... Airport... Transporter... they begin at about $300 & up. The Transporter is $2K. DACs are whatefver you want to pay...

At $2k I wanted more flexibility with other digital sources so I chose to look at a few DACs.. and stayed with the Bel Canto DAC3.

Where ever the conversion from digital to analog occurs is where your bottleneck as I call it, or your limitations reside. Concentrating on getting that area as best you can will pay big dividens... along with the other items I mentioned previously... player, error free ripping, lossless files etc.

A little trouble now, perhaps, but much ease very soon there after... with as good quality as you wish to or can, afford.

Did you put the cd's on the computer at lossless resolution? If you compressed the signal at all, you compromised the sound to start with.

My solution: Get a sound card with digital out (once you've made sure you burned at full resolution). For simplicity's sake get either a Music Hall Raven receiver or Mambo integrated. Both have a built in DAC that is nice. Both will drive the Snells nicely. The Mambo is lower powered but class A rated for warmer sound.

Very easy fix if you are lazy, is buy an AppleTV. It will connect to your Pioneer via HDMI, or you could buy an outboard DAC and connect it via Toslink.

If you want lazy - take a look at my system. I buy a CD online - it arrives in the mail - I open the packet - I throw it in the changer and that is it. Done! CD stays preserved in pristine condition and no messing around with "importing" it to ITunes or some other music server. I play music from the listening position with a wireless keyboard and trackball.

Soo... no one seems to have stated some of the obvious...

First..
Your iMac has an optical toslink out thru the same mini jack you are using as a headphone output. You can purchase a very nice glass toslink mini to std toslink connector cable from Van den hul.I am running this same configuration from a minipc.

With some configuration on the iMac you can disable any of the digital preprocessing and get a pure bitstream out to that toslink connector. Connecting that to a dac will give you very nice audio. I'm using a Bel Canto e.One Dac3. With the toslink out on your iMac... u have a ton of options for Dacs. You're not limited to Dacs that have a USB input.

btw... a headless mac mini would have given you the same solution if you are really using this as a dedicated music server.

The second thing that folks have alluded to is that you need to get the best possible copy of the disk onto your computer. The first part of that is to make a copy (with lossless compression or no compression) using software that will not just take whatever the drives hands it, but rather understands that read errors can occur, and it should try to correct for that by re-reading etc. EAC (Exact Audio Copy) is what i would recommend. Free...and easy to use after a little research. I have that setup to rip a .wav, and an ALAC (apple lossless) copy...so i can put it successfully on my ipod, and have a digital archive copy to convert to whatever other format i would ever want to. Disk is cheap... :-)

The other part of getting a good copy is to have a drive that plays well with EAC.... again to give you the best possible copy. You're pretty much locked in there with the iMac unless you choose to buy an external drive.

Overall there are companies/services as well as standalone very expensive solutions (Linn) that go out of their way to get you that bit perfect copy of the original. (just thought you should be aware of that)

Hopefully that gives u enough to be able to research what makes sense to you.