Even if you plug the audio output into the input you would still be taking a quality loss by passing the audio through a DAC and then an ADC. Maybe if the quality of your hardware is good enough it wouldn't matter, but then you would be limited to only ripping 24 hours of audio per day...

They recently started offering lossless, could you get down to the equivalent of 320kbps?

I grew up on sites like Suprnova, and quickly found I could not discern the difference between 320 mp3s and lossless.

Even now, I only seem to notice if I use a very high end pair of headphones, and mostly with electronic music that has a lot of soft parts with sounds that are in the low or high end of the spectrum.

Bro. Who cares. Ive got bunch of songs like this. The loss makes it more nostalgic