Certain MP3s will not play on my iPod despite reset, mp3 conversion, resetting tags, etc.  What gives?

I had this problem with my last iPod too but it's particularly egregious this time around.  These are mp3s that I ripped from my own CDs and that worked for a while and then just stopped.  It's several thousand (my iPod is 120 GB and I'm a serious music fan).  This is super annoying and I'd like to find a way to fix it.  It will play songs and then just skip some.  If it is shuffling, it also fails to register the song that was played previously? 
This has been an issue for several years with multiple iPod models.  Someone has to have some kind of explanation?  Please?

You haven't mentioned re-registering the DLL's in windows xp which is the suggested fix on Windows XP for ipod's doing this.
Disconnect the iPod from the computer and close iTunes.
Copy the 10 lines below (highlight and ctrl+c or right-click and copy)
regsvr32 /s softpub.dll
regsvr32 /s wintrust.dll
regsvr32 /s dssenh.dll
regsvr32 /s rsaenh.dll
regsvr32 /s gpkcsp.dll
regsvr32 /s sccbase.dll
regsvr32 /s slbcsp.dll
regsvr32 /s mssip32.dll
regsvr32 /s cryptdlg.dll
regsvr32 /s initpki.dll
Open notepad:
1. Start>Run
2. Type 'notepad'
3. Hit return
Paste the text into notepad (ctrl+v or right-click and paste)
Save the file as registerdll.bat on your desktop
Close notepad
Doubleclick the registerdll.bat file on the desktop
A command prompt will appear and these items will be processed. When it is finished you can delete the batch file.
See if it then syncs okay.

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