Why are some of my midi files not playing?

This baffles me, out of a thousand or two midi files I have, about 20% will display an "Mac OS error 208" message saying "this movie could not be opened".
Now, this is neither a movie file, nor a file there should be any problem in opening, since it WILL open, like all other ones, when used inside any music editing programs I have!
Any idea what is up with this seemingly arbitrary & pointless obstacle?

Yeah, iTunes can play them and they have burned to disc but when I play the disc doesn't play all the tracks.
When I open the disc the tracks that won't play have the VLC icon beside them, I thought I may need to convert these in some way.
In addition, when I open up the iTunes Music Library folder on my C Drive the files have VLC icons too.
I'm completely stumped?!?!

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I am trying to backup my friends computer files on a beige G3 (233 MHz). I am burning about 6 DVDs of AIF music files. Most of the files are about 30 - 40 Megs in size. Often I receive error messages on particular files that read:
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1. I first insert a blank DVD-R
2. A message pops up asking my if I would like to create a blank disc image for this disk (I think this is the typical Disk Copy utility window. I say "yes" and give it a name and choose the "DVD-R or DVD-RAM" option. (I am not sure if there are other important settings to choose here or better settings to use but I guessed the other options that seemed obvious. A blank disk image is created with an icon that looks like a DVD disk.
3. Then I drag my chosen files to this blank disc image. It takes about 30 minutes to copy over. Thats when I receive the error message that some files couldn't be "read or written". The other files work fine but it would be nice if they all worked.
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4. Then I choose file/burn in the top menu and the DVD is created. This takes another 20 - 30 minutes. At the very end of the process another message pops up saying:
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To follow up, I have some good news. After following your advice Kappy, it now works very well Thanks! Instead of using the 4 GIG volume for the OS, I am now using an 8 GIG partition on an 80 GIG drive. So now the OS has some room to operate. No disk errors occured on my first DVD
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Why are some of my midi files not playing?

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