Problems transcoding large #s of FLAC files to iPod
Here's the short version of my story:
My iPod was having problems, so I reset it to factory defaults. Naturally, I need to add all 16,500 of my songs again.
About 1500 of these tracks are in FLAC. I have FLAC library support, and Winamp is okay with transcoding FLAC files a couple of albums at a time, it seems, but I left the whole 16000 on overnight.
When I woke up in the morning, 72% of my iPod was taken up, I could find the files on the disk, but the iPod refused to believe that it had any of my songs and playlists. When I disconnected and reconnected to Winamp, nothing showed up either.
So I reformatted again, and tried doing it in smaller chunks. All the tracks A-H went onto my iPod fine, but when I got to the letter 'I' (which contains many albums by the same band in FLAC), the same problem happened: the files transferred, but the iPod software would not find them. The A-H songs stayed on, but the 'I' songs took up space but were nowhere to be found.
I am currently transferring 15,000 mp3 format songs to my iPod all at once to see if they work. If they do, I'll know the problem is exclusively with FLAC files not being transcoded/transferred properly. If not, I'll know that it's not only the FLAC files, but that Winamp and my iPod have problems with any large number of songs, regardless of format.
Has anyone else had similar problems with FLAC and iPods before? If so, what's the solution?
tl;dr: Trying to transfer large number of songs, FLAC files keep screwing up the process because Winamp can't process lots of them in succession. Help!