Songs "missing" from playlist still in library

I've seen similar threads but my issue is slightly different. I do apologize if this is a duplicate post.
In many of my playlists, a song will now be marked as missing by an exclamation point.  However, the song is still in the library and I can manually locate it.  This is happening to too many songs (70 at last count) so it is a PIA to fix.  Any ideas how to automate this? Suggestions on how to stop this from happening (this isn't the first time)?
I haven't moved any songs or made changes to song names or libraries. The songs are in the same place and when I click locate for the first missing song in the list, iTunes goes directly to the right folder.  For each subsequent song, I've got to point iTunes.
Thanks!

Not a Sony Vaio. I have one of the first iPods. It was a gift. It's not that songs disappear from the playlist in the iPod, but from playlists on the computer. They are in the music library and I have to copy and paste them back into the playlist I want them in. I haven't lost any from the music library, fortunately.
The playlists (I have a bunch of them) are blue with a music note. The songs in the playlists have checkmarks next to them, and are all checked. They just drop out of a playlist every now and again and I have to copy it back in. I can go for a while and think "hey, I haven't heard X in a long time". And sure enough it's dropped from the playlist in the computer, and I have to copy it back in from the library, then resynch the iPod. Really weird and mildly annoying.

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