Moving my itunes library onto my new ipod

I get a brand new 30 gig video capable ipod. Honestly I don't care about the video I just want the album covers as I browse my music. I've gone to great lengths to convert my old CD and tape collections to mp3 and even in spite of losing some hard drives over the years still have most of it. I supplemented JUST SOME of my still owned tapes and cd's out of convenience from Limewire and other such sources... but this is a very small part of my collection. SO... My legal library is mixed with all kinds of conversions as tech was available over the years is now in itunes. I buy this brand new spiffy 30 gig video ipod from the apple store yesterday on Michigan Ave.
I get it home and plug it into my stand by home (little used) imac... (purple if you must know) and proceed to watch itunes sync to it. It finishes and I look at my ipod... nothing in any music category at all... I reset it and do this again... nothing... mind you this is an imac running 10.3.9 and with itunes 7.1.1 Then I go to the support pages here and read some things on the internet that basically say if you didn't buy it from the apple itunes site or rip it with itunes... it won't be recognized by your ipod. Is this really true?
I can't put my legally purchased original copy of aqualung that I took the time to convert from tape via a convoluted mess of hardware into digital... let alone ultimately mp3 format... on my new nearly 300 dollar ipod???
My ipod shows in itunes fine and even shows the music (greyed) and the space it is taking etc. in itunes.
But if you scroll into the menu on the ipod,for music, there is nothing.
I had a 20 gig old ipod and the drive on it crashed but it didn't have all these rules etc. i'm reading about with it.
It was great until it died.
What am I doing wrong?
I really can't sync my library to my new ipod unless I repurchase all this music?
Should I take a single box (of many boxes) of my CD's and tapes to Michigan ave. and drop them on the door to illustrate how much music I actually own?
Why does itunes say I'm sync'd and even show the space it took up on the ipod and yet not allow me to play anything as if I had no music on it?
HELP!

Have you tried just resetting your iPod while it is connected to your computer?
I am assuming your iPod is showing a large amount of data in "Other" and nothing in music?
The problem may have to do with ID3 tags in your MP3 songs and not in the format of the songs, but you might right click on one in your iTunes, click Get Info and post the results here.
There is nothing that says if you didn't rip it with iTunes or buy it from iTunes it can't be on the iPod. There are posts here where people have used other converters and the resulting files have bit rates that cause problems for some iPods. And you can't play protected songs from other sources on the iPod with first burning them to CD and then ripping them. Whatever you read on the Internet was not correct, and you probably aren't going to collect from that Nigerian bank either.
Incidentally, acquiring music from Limewire and "other such sources" would make your statement of "My legal library" not quite true.

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