Why does itunes keep dropping my devices and files

Everytime I set my iPods asides for a few weeks and then reconnect them to iTunes they will not sync.  iTunes flushes all the content I've loaded from CD's <1,000 songs plus audio books.  iTunes wants me to re-register and reload everything.  This has appened three times in the last year.  It happens on both my Windows and OS X machines.  I have an iPod Touch and an iPod classic.  ITunes refuses to allow me to keep both devices and computers in sync.  Before I spend the two plus days to reload again I would like to know what the heck is going on.

Why? Sony Viao by any chance? That comes with some media scanning software which has a habit of interferring with iTunes when it save files, resulting in a corrupt or missing library. Anti-virus software may also possibly be a cause on occasion.
See this User Tip for an effective backup strategy.
I've also written a script called DeDuper which can help remove unwanted duplicates. See this  thread for background.
tt2

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