Hopelessly mid fi?

I'm not sure about the claim that a reputable CDP will outperform a computer based transport. I would imagine the most of the difference will be in the DAC and the downstream. That's not to say that all transports sound the same, but the difference in the transport is probably a lot more subtle than differences in DACs for example.

I have recently acquired Accustic Arts DAC, and it definitely improved red book over my Linn Unidisk SC. You might want to consider adding a DAC as well.

Its a bit difficult to answer your question when you have "intentionally withheld" the imformation on your CD player, but nevertheless.

In my experience, the difference between compressed files and Lossless, is very clear even just listening through the iPod itself - it shouldn't need a highly resolving system to discern this difference (though I imagine the rest of your system is actually pretty resolving anyway). Likewise, when I had my iPod docked in an Arcam dock feeding an analogue signal to my amp, it was clearly inferior to my mid-price CD player and that was playing lossless files. I found the best way to listen to my iPod was through the Wadia 170i Transport which feeds a digital signal from the iPod to my outboard DAC via a digital jitter suppression device. In this context, the sound from the iPod was equal to the CD player with the same jitter reduction device and the same DAC. Please see my review of the Wadia 170i here on A'gon for more information.

If you can't hear the difference between the various sources you described, I wouldn't be looking to spend $2k to try and hear the difference - if you enjoy the sound of any of the combinations you already have, be happy and buy more music. :)

If you are fixed on upgrading your source, I would look at investing in a decent DAC (some outstanding ones at under $2k) which would provide a significant upgarde to your CD player and SB. Alternatively, the Wadia iTransport plus a decent DAC is another outstanding option but get a DAC that does its own internal jitter reduction.

Computer drives are reportedly superior transport mechanisms. Evidently the data the computer uses must have very very low jitter and a clock that ensures an accurate constant data stream.
I assume all this is not actually the reader but the correction elements.
I have always been surprised how good computer generated music sounds even when burned onto a CD for use in an "audiophile" CDP.
Unless you have a very special CD player the transports invariably fail before any other elelement. An older CD player even a once great player that uses one of the 2 common transports, will start sounding progressively worse over time.
I recommend borrowing your audio nut buddy's almost new but burned in just this week EMM,Meridian, Esoteric etc. player and do the comparison.
If you have an old player that still works lying around compare it to the name intentionally witheld player. Suddenly it will sound fantastic. You will save serious money that way. Then buy the Wadia Dac.

Were the lossless files ripped error free?

If not night and day diffs, the replay should at least sound more rounded and natural with the lossless files.

The comments here on a dejitterizing and worthwhile DAC are true! IME Either way... PC audio or disc player.