Files not playing properly

I've never had this problem in the past but recently (in the past month or so) certain songs in my library will play properly up until a certain point and then iTunes stops responding. Once that happens I can't do anything on my computer until I force iTunes to quit. I've tried installing the newest upgrade and it hasn't helped. I've tried playing the files in other media players and encountered the same problem. It's even been known to happen to files that have just been added. I tried to create an AAC version of one of the files as an experiment and it gave me an error message (-3). I should also mention that I keep my library on an external drive. It has been accidentally unplugged once or twice while a song has been playing but I have no problems with the songs that were playing at the time. Any advice is appreciated.

Thanks for replying, William.
I'm using Robohelp version 8, HTML Help. The problem only occurs with the CHM file. Within the help, it checks out perfectly (when I click the links, Windows Media launches and the correct video starts playing).
I'm not sure where to place HTML code -- I've seen a few other examples that say to select Insert > HTML Controls > Tag. However, I haven't got a "Tag" menu option. Also, the Justin Cook code is for starting a video upon entering a page, which I do not want -- I want users to be able to select a control/link to view when they want to view...
Thanks again. I'd appreciate any other advice you can offer.
- Wendy

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