"Copying and pasting tracks to individual files and then renaming them"? Wow, that does sound labored. Vinyl Studio has windows to enter the names and times of the tracks in the album sequence before (or during) digitizing. After recording is finished, breaking the tracks is simple; you just go into the sound file (it's rendered as a waveform graph like you might have seen in GarageBand) and use your cursor to edit or break it. Sometimes I've altered the playback to my liking, by giving more or less space between tracks.

Btw, I just finished that Stereophile piece, and the gist of it seems to be that many of these programs are great once you get the hang of them, but for most non-techies they're also really clunky and non-intuitive, so there's always a learning curve. I actually didn't find that to be the case with Vinyl Studio. On the other hand, the author of the Stereophile article, Michael Fremer, seems to have experienced all kinds of speed bumps before getting into the Pure Vinyl program, whose stated aim is to make the digitized file sound better than analog with the help of 24-bit/192kHz resolution capability and a RIAA equalization curve option. If any Outlaws wanna try it themselves, "Pure Vinyl" is available for a 15-day free trial at channld.com/pure-vinyl.html.