Sorry I can't answer your question because I don't have a Fuze or use WinAmp but the way you worded your post suggests to me that you transcoded (converted) your previous library to FLAC?
Please tell me this isn't true.
I have a Fuze, but I just transfer my files over as if the Fuze were a hard drive. It's a little bit annoying, but one less program to deal with. As far as "switching" your library to FLAC, you don't mean that you went from mp3/aac to FLAC do you? Going from a lossy codec to a lossless codec will just increase the size of the files while doing nothing to the sound quality...
Don't worry, totally deleted the previous versions and re-uploaded everything as FLAC. I ended doing what usf09 mentioned and transferring everything manually. Took forever, but oh well.
Yeah, it's annoying, it took me a couple weeks to split everything up. I used A,B,C... for my files, then went by artist. But now, every time I need to add new songs, it's pretty simple. I've though about going through Media Monkey or something like that, but this works fine for now. Good to hear you re-uploaded, enjoy the Fuze...sounds very good, IMO, even better with Rockbox (though I decided to wait until a stable version is created before keeping it as my firmware)...
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