GAPLESS PLAY BACK IS KILLING ME!!!!!

I really hope someone can help me out there.
I recently had to rebuild my itunes library after a severe hard drive crash, and in doing so had to rip a lot of my CD's again.
upon opening itunes it starts looking for album covers and then it started doing gapless information.
Here is the real issue, it just stalls!!! over and over. The never ending spinning frickin rainbow!! I have to force quit itunes (which by the way always says "itunes not responding")
I've checked for corrupt files by moving them backwards and forwards between my main drive and an external drive to capture any bad eggs. I found a couple but jeez this is just ridiculous!
I know I can't have that many corrupt files, god knows I've thrown away enough as a precaution. But my patience is wearing very thin. If anyone can help I'd really appreciate it
Macbook   Mac OS X (10.4.9)  

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