What is the missing element?

My pc audio setup currently is as follows

PC (Lossless audio through Jriver) > V-link (first model) > Rega Dac > Jolida JD1501 > KEF LS50s

The Rega was probably the first component I bought that completely transformed the sound of my system. The difference it made was simply huge.

I then added the v-link to support higher resolution audio through the s/pdif connection. Again, the sound noticeably improved. The soundstage was bigger, and the music just sounded fuller. Without the v-link the music sounds quite a bit smaller through the usb input.

The Kefs were the next big leap forward for my system. I simply cant believe how big a sound these tiny little speakers put out.

Now, originally most of my listening was through the setup listed above. However, the addition of a thorens TD-160 has gotten me into vinyl in a big way and now I really don't like the sound of digital. By comparison it sounds like congested chaos, has a rough texture (especially noticeable in voices)and overall is just very brash sounding. I simply can not stand it at loud volumes. Nothing like the polite orderly smoothness I hear on vinyl which constantly has me turning up the volume.

I had all but completely switched to listening to music on my turntable while the rega was relegated to streaming pandora or youtube as background music and always at low volumes. Then, some time spent with a naim cd player reminded me just how good a digital source can sound. So my question is how can I bridge the gap? I have been reading a lot about jitter and I am wondering if that is holding the rega back. I've read that the v-link measures at right around 400ps while other digital transports like the audiophilleo measure well below 100ps. Would replacing the v-link with an audiophilleo or another s/pdif converter give me the sound I am looking for? Is the problem with the nature of computer audio itself and I should just be looking for a good CD player? I am slowly driving myself crazy over this.