I use EAC (Exact Audio Copy) to rip the music. I use both Windows Media Player (OCD default) and JRiver Media Center for playback. Funny you mention Audacity, I do much editing with it and scan media afterwards. I can't recall anything in mp3 format not transferring. I keep wav files for uncompressed sound quality. I stay far and away from anything Apple because of hardware compatibility.

Seems the root of this problem (and I had mentioned this to Andrei long ago) is once again Microsoft blundering. I noticed the issues going from XP to 7. The ability to edit audio files in 7 was almost non-existent. I searched high and low for a resolution and from the MS forums it was concluded that it was a known issue the was never addressed. Typical MS, lets drop 7 and start with 8. Now, they're trying to come back with a 'solid' version 10 to sweep the shortcomings of 8 under the rug. Again.

My collection is at over 8,000 total records. As this point I'm not sure what to do. Of course sound quality is my greatest concern.