Mixed Up / Missing Tracks: Is Anyone Else Having This Problem?

[squagmire]

First, the specs:

I'm on XP SP2, Athlon 5200+, Asus M2N-SLI Deluxe Mobo, 2GB of DDRII 800Mhz RAM.
Running iTunes 7.0.2.16 and Winamp 5.32.

My iPod is a Black 80GB, brand new. Have only been using it for three weeks or so.

During this time, I've been transferring and transcoding songs onto the iPod using Winamp. I have a pretty massive collection, nearly 60,000 songs, most of which are in FLAC, OGG, and MP3 format. I use iTunes only to manage the iPod playlists once the tracks have been transferred / transcoded, but obviously can't use it to trancode, since it won't even see the FLACs or OGGs in my collection.

Transfers are pretty slow, even when transcoding isn't necessary, so it's taken me a lot of time over the past couple of weeks to populate the 80GB drive 3/4 full. However, just today, I noticed that some of the tracks, when I play them, aren't actually there, and some other track starts playing instead, requiring me to delete the "dummy" non-existent tracks and re-transfer them to the iPod.

I'm finding this is the case with numerous tracks, and it's really beginning to tick me off. I've been playing in "shuffle songs" mode every day, and didn't notice this problem before today. I can't find any "verify tracks" or "rebuild database" options in either iTunes or Winamp, so there doesn't seem to be any way to get rid of all the dud tracks automatically. Why is this even happening?

What's worse, iTunes is telling me there's a firmware upgrade for my iPod (1.2.1) but it can't connect to the update server to perform the upgrade.

Does anyone have any suggestions here? Is this a known bug that the firmware upgrade will fix when I'm finally able to download and install it? Or third party apps that might do the trick? I tried PodUtil, but that didn't seem to have any effect. I really don't want to have to reformat and start from scratch, as it will be 2007 before I get the frikking thing filled up with songs again.

[dcorban]

So you have invested a lot of time over the span of several weeks and you don't keep a copy of the transcoded files?

If you were maintaining a library on your computer (of the transcoded files) could could easily resync or "consolidate library" in an attempt to correct the problem.