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I'm not sure if there's any software around that will automatically label a track that you've say recorded youself - even when you've used the optical output from the physical player (not the computer) into an optical input on the recording device.
If someone knows some software that performs this trick I'd be really pleased
not sure of any, but as you say winamp is good, i have found it to be 98% reliable for finding track lists. not so great at album art but thats easily solved with google images.
and as long as you play the album in winamp you can get it to search for the info, you dont have to have ripped it in winamp.
In winamp playlist highlighting all the tracks and right click /send to /autotag will generally sort it out, i then use wmp3tag and open the folder highlight the tracks and click tag to filename ,this changes the file names from track 1 track 2 etc to the tag you just created in winamp.
it sounds complicated but is really very simple once done a couple of times.
you can even set the parameters for the way it shows ie.
track number /artist/track title /cd number etc and you can rearrange the order these show in wmp3tag and in how it displays in the playlist in winamp.