Match and sync music on 4 devices

I have itunes on 2 different computers (Windows), I have an ipod classic, and an iphone 4s. how can i match and sync all songs to all 4 devices? My song counts are different and i dont want to delete any that are not on the other devices. But with so many songs, there is no way i can attempt to match them up. Display Duplicates only works in tunes but is greyed out for ipod.
I thought this was supposed to be easy!

iTunes Match manages your music once enabled, this takes over from the original synchronised Songs.  Essentially it is your choice to either remain with manual synchronisation or switch on iTunes Match.
Provided your source library holds all your Song files and is securely backed up, you will not loose any Songs by enabling iTunes Match.  Whether you prefer the sevice enabled or switched off is very much a personal choice.

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