Songs transferred to Ipod will not play in Itunes and don't show in Ipod

I have had a nano for a good 6+ months and have yet to be able to fill it up with music. Under 200 songs it is a crap shoot whether or not the songs will show up after I eject it. If I load 200+ songs to the Ipod one of two things happen. 1. After ejecting the Ipod none of the songs i loaded show up on it, and after linking it back to the computer, itunes tells me that it must be restored. 2. a good number of songs will not play but are skipped over. The album art shows for a split second and goes to the next song. The next time I plug it into my computer it says that It does not recognize it and forces me to restore it again.
I have done the following among other things.
1. Repeatedly restored my ipod, this does not help.
2. Re-installed Itunes and Quicktime.
3. Loaded only AAC files.
4. Turned off Spy Sweeper while before plugging in my Ipod and load songs.
5. Disabled Norton Anti-virus.
6. Confirmed how I am ejecting it.
6. Replaced my Ipod once.
7. Bought a new computer HP Pavillion a1630n.
8. Invested well over 40 hours of my time trying to get this thing to work.
I have over 200GB of music which and I cannot get much more than 2GB on my 4GB Ipod without a problem. As of this writting I have restored it 6 times, after each time I drag my songs to the Ipod icon, when it is done loading, I press the eject icon next to the IPod and each time I click English-->Music-->Artists--> and after that all I get is All-->All-->Nothing. I plug it back into the computer and have to restore it and start over. I have had the same problem on two Ipods, and two Computers. I want this to work so bad. Help Help Help.

The exact message that I get each time I plug my Ipod back in states, "iTunes cannot read teh contents of the iPod "MILOPOD." Go to the summary tab in iPod preferences and click Restore to restore this iPod to factory settings."
I am continually restoring my Ipod over and over again reducing the number of songs on it over and over until I get lucky enough for the songs to stick. Only about 100 or so will regularly stick. I am now restoring it for the 7th time.

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