Thanks for the very quick response. Here's the file:
Media Center Registered 11.1.191 -- C:\Program Files\J River\Media Center 11\
Microsoft Windows XP Workstation 5.1 Service Pack 2 (Build 2600)
Intel Unknown 1998 MHz MMX / Memory: Total - 1032 MB, Free - 567 MB
Internet Explorer: 6.0.2900.2180 / ComCtl32.dll: 5.82.2900 / Shlwapi.dll: 6.0.2900 / Shell32.dll: 6.0.2900 / wnaspi32.dll: 4.71 (0002) , ASPI for Win32 DLL, Copyright © 1989-2002 Adaptec, Inc. / Aspi32.sys: 4.71 (0002)
Ripping / Drive H: MATSHITADVD-R UJ-846 Mode:Normal Type:Auto Speed:Max
Digital playback: Yes / Use YADB: Yes / Get cover art: Yes / Calc replay gain: Yes / Copy volume: 32767
Eject after ripping: Yes / Play sound after ripping: No
Burning / Drive H: MATSHITA DVD-R UJ-846 Addr: 0:0:0 Speed:24 MaxSpeed:24 BurnProof:Yes
Test mode: No / Eject after writing: Yes / Direct decoding: Yes / Write CD-Text: Yes
Use playback settings: No /
I should mention that I'm running MC on a Mac running Windows (I had the same problem with my PC) and am now using it with a 60GB Video and a 4GB Nano. Both experience the same problem.
The problem with trying APE is that I have over 5000 files and this issue with the iPod is occasional and I haven't been able to deliberately induce it. In other words I could convert a subset of files to APE and only transfer them but there's no way of ensuring it would work consistently (it may work for a month and them suddenly stop). It's not so much a problem with the Nano as it obviously holds a lot less so takes less time to sync after the initialization, but the 60GB takes around 8 hours.....