Songs Purchased from iTunes Won't Play on iPod

I purchased some songs from iTunes. They play perfectly fine on my computer through iTunes. However, when I disconnect my iPod from my computer and try to listen to those songs with my headphones or in my car through my iTrip, my iPod just skips over those songs and goes to the next song in the shuffle. Or when I try to play the whole album, it'll show 1, then 2, then 3, and so on...it skips through the whole album then ends up at the main screen without playing a single song. I've tried deauthorizing/reauthorizing my computer, I've restored my iPod many times, I've cleared my library and restored it with my backup files, I've uninstalled and reinstalled iTunes, I tried using an old updater to get the previous iPod software, but that doesn't play vidoes, and I've done all of the above on three different USB ports.
I've called Tech Support many times and they keep telling me the same thing and nothing works.
So, I finally made my way into traffic-congested Tysons Corner to the nearest Apple Store and all the guy could tell me was that the file was corrupted and to re-download my purchases. So, I go back home, get on iTunes, search for my purchases and I'm told that my purchases can only be downloaded once.
OMG! Someone help! Is there anyone out there having the same problem!??!?!
Dell Dimension 4550   Windows XP  

Enable the iPod for disk use. See How to enable disk use.
Go to "my computer" and from the tools menu/folder options/view tab, enable "show hidden files and folders" in the advanced settings pane. Open the iPod in "my computer". Look for a file called "iEKinfo". Is it there? If so, make a copy of this file and save it somewhere easy to find (the desktop for instance). Do this also with the "iTunes DB" file. Don't worry if you can't see these files.
Create a new administrator account. Log out of the current account and log in to the new one. Then restore the iPod to factory settings.
Open iTunes, connect the iPod and set the transfer preferences to manual transfer. Then download the free single of the week from the iTunes Music Store. Verify that song plays in iTunes.
Now, drag this song only to the iPod, and eject the iPod from iTunes and disconnect it from the computer.
Does the song play on the iPod ok? If so, log out of the new user account and log back in to your normal one (the one you have issues with) and reconnect the iPod to the computer. Keep manual transfer selected for the moment. Drag some of the older purchased music (the ones that wouldn't play before) to the iPod.
Eject the iPod and disconnect it. Do those songs now play ok?
If not, first try this step.
Delete the SC Info.sidb file. Open iTunes again.
Now transfer some of the affected music to the iPod again. Does it play ok?

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