Sometimes songs sync, sometimes they don't

I have my iPod set to sync all music and playlists. Everytime I sync random songs are left off my ipod. I just synced it 3 times in a row and had different results. Some of the songs left off are ones I purchased, and others are off of CD's I've uploaded to iTunes. For example, the most recent CD I bought I uploaded to Itunes the other day. I went to play it on my iPod and only 1 song from the entire CD was on my iPod. I synced the iPod, and then 2 songs from that CD appeared. Today I after syncing several times I now have a 3rd song from that album. All songs play fine on iTunes. What is the deal? I'm missing over 100 songs from the 1700 that should be syncing. I can't find any connection between the songs that aren't syncing. Sometimes my favorites playlist has all 25 songs, sometimes it only has 19 songs. Again, my iPod is set to sync ALL music and playlists. Anybody ever hear of this before?

I have the exact same problem. I have my iTunes library with 568 songs, and four videos yet when I sync it will start to sync but stop and says it's okay to disconnect meanwhile no songs were synced at all. I have 513 out of the 568. Strangely, when I kept syncing for a while it brought me down to 125, then another time to 299 and now 513. And for some reason when I synced, about 55 files were "not found" for no apparent reason. I checked the files and they were there. I even checked on my siblings iPods and the exact same file was on there perfectly fine. It is getting me really ticked at this point. Does anyone have a solution?

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