iPod Songs Not Showing On Ipod

[KOX KingOfXbox3]

I am having a problem. On my itunes it says there should be 24 songs in the playlist but on my ipod it says only 23? Is there someway to fix this as it is doing it for more then one playlist?

 

[KOX KingOfXbox3]

I know there is nothing wrong with the song data as I have this one song in more then 1 playlist. And it shows in 1 playlist but not in the other for some reason?

 

[Crp5]

I know there is nothing wrong with the song data as I have this one song in more then 1 playlist. And it shows in 1 playlist but not in the other for some reason?

Having the exact same problem on multiple devices. Song format doesn't seems to matter either. I have acc, mp3 and iTunes purchased music that will / won't show up at random. This is across 3 new mac's. MBA 13" for wife, MBA 11 for me and iMac for kids. Syncing to IPhone 4, IPhone 3GS, IPod Touch 3 gen and 4th gen. Doesn't make any sense and there is no pattern I can follow.

The play list (actual) on device even changes count after new sync. Maybe one or two songs but changing! Very frustrated!