With each download/upgrade, I am losing more songs

I should have been concerned about this earlier, but periodically, some of my tunes disappear or I find the tune and iTunes says that it can not find the original tune. Neither can I. I put my playlist on a removable hard disk drive. Everything worked fine for quite a while; then tunes started disappearing. At first I did not draw any connection to the upgrades; but with this latest mess, I started looking around and found my tunes broken down into several dated files/units which now appear to be a result of prior upgrades. How do I get out of this mess?
Thanks for any advice.

Sync ith only one computer. When you sync with the second anything acquired from the first computer will be erased. Syncing back with the first computer will erase everything synced from the second computer.
Put all your stuff on one of the computers and sync with only that one.

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