If so I think I will give up on it.

I think something that resides on the iPod and works cross-platform would be awesome. Both Yam. and Floola say they do that.

I abandoned Floola since it wouldn't convert WMAs on the fly, and seemed to give me spurious characters. I had to delete a bunch of spurious characters from artists, genres, etc. Also, I had to delete duplicates, not sure if they were from my collection or from the software doing that.

I got around 14,000 files on the Classic, still have probably 6000 to go :) Floola said the WMAs were converting and installing, but they never showed up. Not on Floola, not on iTunes.

I uninstalled Floola, then tried to load Yam.

Here are some frustrations w. Yam.:
I wanted to be sure that everything would go OK, so I connected to another comp. that still had iTunes.
Using my new Classic 160 gig with the older ver. of Itunes(8.0.something?) I got an error message that said that iTunes was too old to support my Classic.
I went to OldApps.com, installed iTunes 9.21.1.
Now Yam. won't recognize it.

I get the same error others are complaining of. However if Floola is simply a newer version of Yam., I'm likely to have the same issues I had with Floola.

Should I give up now?

Spectraman

This is one of the worst problems to have.

I had the same situation, and it ended up that I lost many files but I had backup copy, so It was not that bad