Playlist on ipod doesn't add all the songs from itunes playlist.

I made a playlist on itunes and then synced my ipod and not all the songs are on the playlist. They're on my ipod just not on the playlist. I don't have iTunes Match and I've tried pretty much everything. I bought all the songs either with CDs or through itunes. It's annoying all the songs are on my itunes playlist and then they're not all on my ipod playlist. I have 1000+ songs on my playlist and I hate having to find what songs are missing. Is there a way to fix this. I even reset my ipod and did it again and it still dose it. Regardless if it's on manual of not. :( someone please help me fix this. I have the iPod touch 5th gen

Ok, I deleted the two files and upon startup iTunes did run that search wizard for music files. However, it only found 4 songs that are located on local harddisks, and did not (as far as I could see on the network status) even try to search on the network harddisk.
One more thing though, that I forgot to mention before. I tried to solve this situation by installing an earlier version of iTunes... 4.6 i think, but when I tried to run the program it told me something like "Cannot read the file iTunes library.itl since it was created by a later version of iTunes". Where can i find that file, and should i remove it and try to add the songs with iTunes 4.6 instead?
(Thanks so much for all your help!)

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