I've owned a PS Audio Digital Link III and a Musical Fidelity V-DAC. Both are at or below your price point and both sound very good.
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I have a Rotel RCD-1072 and since January also have a Squeezebox Touch ($300). Lately I don't listen to the CD player anymore. Sound is the same - both going analog out into a preamp). So if you had nothing I would say go for the Touch, and later add a DAC.
Do you want to be able to do high resolution files?
If no, maybe an MHDT Havana fed from the computer?
If yes and since you have a computer, you might want to consider feeding through USB an Audiophileo USB to S/PDIF converter, and from there a hi rez DAC without asynch USB. Maybe an rDAC? Don't know much about this price range. Lots of good options in the $1k range, though.
"I am not worthy of calling myself a true audiophile"
Yes you are and don't argue with me :-). A Scott 222 and the Omega 3r's (I've owned both) = MUSIC. I've auditioned some "marquis audiophile" names that weren't as musical.
I'll let others advise you on the DAC's but I think you will be pretty happy with your result. Good luck.
Thanks everyone. Too many choices! I guess that's a good thing. I might check out the Music Fidelity V-DAC, but want to do more studying.
Onemug, okay, I won't argue with you. I guess I associate audiophile with a bigger budget than I have put out, but I have other expensive hobbies including a wood shop. Just a FYI. I bought my Scott here for $275 in maybe 2005. I had hotglass fix it all up and he told me it was actually one of the earliest 222's and was biased close to Class A - as such a somewhat unique and above average Scott. I have only heard a 222D and it was not even close, so with zero knowledge I guess I lucked out.
I second the PS Audio DL-III and the V-Dac. However, if you will only be connecting the iMac to the DAC, I recommend that you strongly consider USB only DACs, such as the HRT Music Streamer II+ ($350) and the Centrance DACport LX ($300) which will give you even more bang for your buck in your particular application. The computer digital interface is tricky, as there has been a lot of development in USB technology in the last couple of years, and these two USB DACs represent the results of two different approaches.
Keep in mind that many folks here (including myself) will rave about the value of the PS Audio DL-III and the Musical Fidelity V-DAC. But the praise most often refers to the performance of these DACs using coax or optical inputs, not the USB. If you plan on using USB connection, I would give the HRT II+ a strong consideration. There is also a new V-DAC-II out, which I believe now has an asynchronous USB interface, and thus might also be worth your consideration.
IMO, save your money and get a really good dac like the Wyred-4-sound dac1 or dac2. in the long run, you will actually be saving money. i did exactly what you are going, starting small then moving up. a nice cheaper dac is a cal sigma or alpha dac. i then moved up to an audio research, then a manley. after demoing many new dacs in my own system late last year (ayre usb, bel canto, stello, audio research,and a couple others, I bought the wyred 4 sound dac2 to pair up with my mac mini running pure music. i had a $3000 classe cd player which was rated very good, and my mini/dac2 combo is much better. i sold my cd player a year ago and never regretted it.
instead of buying a cheaper unit now, then selling it for a loss to buy something better, and doing this a couple of times, just get a great dac now and enjoy it.