RE: bought ipod classic, and have alot of questions !
For your tagging problems, I find that it's actually better to rip my stuff using EAC and tag them with that. I also prefer it to iTunes for ripping, because it can use any external encoder you like - LAME is widely recommended, using the -v0 setting gives you pretty much the highest quality.
As for high quality, I like high quality too. But I don't watch videos on my iPod. I've used the Videora convertor with PSP Video 9 for PSP before, it was an okay tool.
If you have the same file size as an MP3 Danny, then you must've seriously sacrificed video and audio quality...
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