Moving music across 4 devices?

Ok this situation gets a bit complicated so I'm gonna explain how everything is right now
A few years ago I changed from a PC that was pretty much dead(I'll call it PC1) to another PC(I'll call it PC2), and very recently I changed to a Mac. I have an old 4th generation iPod nano, and an iPhone 4s.
I no longer have ANY access to PC1, but theres a good deal of music from that PC on the iPod nano, not all of which was purchased on iTunes. I was using that with PC2, because it was easy to load music at that point without forcing the iPod to sync and lose the music that I no longer had access to, but I never figured out how to move the music that was from PC1 to PC2.
Then I carried on getting music on PC2 both from iTunes and not from iTunes, and put it on my iPod and iPhone. Later my PC had a pretty bad melt down and I had to do a factory reset so I lost some non-iTunes music, but restored all my iTunes music, and everything on my iPod and iPhone was fine, because, like I said, with that version it was easy to avoid fully syncing and losing everything from my mobile devices.
Now I have my Mac and I've purchased a few albums from bandcamp(a non iTunes store) and I have that in my library along with all my iTunes purchases, but I can't add them to my iPhone because now my library isn't exactly the same as PC2, so I can't check the "manage manually" box on my Mac without syncing my iPhone and losing a TON of music.
So basically my problem is that I have 4 different devices and none of them have the same music on them and I cant manage music from my current computer and I don't know how to fix that.
I know keeping the music from PC1 is probably a lost cause but if theres any way I could do that it would be awesome.

Three words: backup, backup, backup, or you will lose your data.
See these user tips: Recovering your iTunes library from your iPod or iOS device and Syncing to a "New" Computer or replacing a "crashed" Hard Drive

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