Songs not copied because they cannot be played on an iPod

[TheWraith]

I attempted to search the forums regarding this issue, but needless to say, the vBulletin forums are less than intuitive. Frankly, I think they're the worst search subroutines I've seen in a message system, ever. But, that's a separate issue, anyway...

I have two songs that won't copy over to my iPod stating:

Some of the songs in the iTunes music library, including the song <song name>, were not copied to the iPod, <ipod name> because they cannot be played on an iPod.

One of these songs are a protected AAC file I purchased from the Apple music store. The other song is a compliation from a 'dance mix' CD purchased years ago. I haven't been able to get either of these songs transfered to my iPod, using iTunes for Windows.

If anyone can provide any assistance, I would appreciate it.

[TheWraith]

Update:

After about 5-6 redocks...and re-syncs, the one Protected AAC file copied over without any further issues. I didn't do anything different. I didn't do anything special. It just self-resolved.

I noticed the 2nd file was an MPEG-1, Layer 2 format. I converted it to AAC and it then copied over without further problem.

My last remaining mystery, is that my iTunes states I have 5 songs more than my iPod says I have on it. It's set to automatically sync. Any thoughts on the best way to determine why the counts are exactly mirrored? Some of the songs might have really long names, does the iPod have any limitations in that regard? I haven't received any other notification other than the two songs I mentioned before not copying. However, my song count between iTunes and the iPod aren't equal.

I'm not entirely sure how to determine why.

[TheWraith]

Update:

The 5 song disparity was caused by multiple conditions:
1. Duplicate songs.
2. Converted songs.

I had a few songs I must have imported more than once. These were easily found by searching for "(1)", etc. since iTunes names them in that fashion. Removed all duplicates. I was still a few songs off, which I determined to be the cause of having converted some songs to AAC format. This process doesn't actually convert the original file, it copies the original file, leaving you with two files of the same name...different format. I deleted all original files that I converted to AAC (from MPEG), and now my lists are completely synced up.