I went through an enlightening exercise last week. I digitised three sets of 7 tracks of various genres using a different cartridge for each set. The purpose was to play these into a friend's system for comparative purposes without taking my turntable and phono stage over. For digitising I have the balanced output of my EAR324 permanently wired to the balanced inputs of a Digidesign 002, using Pro Tools as the recording platform.
The cartridges were, in turn, a Koetsu Rosewood Signature (Paratrace diamond from Expert Stylus), Ortofon MC30 Super II (Stock) & Denon DL-103 (Paratrace diamond and sapphire cantilever from Expert Stylus). Levels were matched using the HFN test record - Side 2, Track 1 set to -6dB. Recording was at 48/24, chosen to match the best available output of his G5 Mac. After capture in Pro Tools the dual-mono files were combined in Bias Peak LE 6 and saved as AIFFs. That was the extent of post-processing. The replay was from iTunes 10 via optical to a Musical Fidelity XDac V3. Apart from the files I took the records over to compare directly to his replay, from a Rega P25 / RB700 / Sumiko Blackbird.
The comparisons were interesting but it soon became apparent that the "live" playback of the records thrashed comprehensively any of the digital versions. It wasn't too subtle - the soundstage was flattened and a lot of impact and general excitement was missing-in-action. I've heard his entire front end including phono stage on my system and I know I wouldn't choose it over mine, as nice as it does sound.
A bit of a lesson in the (lack of) transparency of digital recording.

