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At first i thought it was the FID limit, but i only have like 1600 songs on my player. could that really be it?

Definitely not it.

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If i delete a file, then try to add the file that failed before, it works fine.. so it appears to be reaching some limit, but what i have no idea.

It's removing the file from the "good" hard disk, thus leaving space for the new song on the same good disk. As soon as that's in place, then it tries to place the next file on the "bad" hard disk, and then fails. See here for a description of why.

As was previously stated... From the looks of your boot log (by the way, click here to find out how to produce a non-scrambled boot log, as was previously stated, hyperterminal has a clipboard bug and you should do a capture text instead), you've got problems with one of the disk drives. It's either the cable, the jumper, the IDE header, or the drive itself. Follow that link in the prior post and carefully go through each part of it.

After you solve the disk drive trouble, you might need to do a FSCK and a manual database rebuild.
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Tony Fabris