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I'm not a big ipod fan, but look at them from time to time for friends and clients. I think once you delete the files, you also need to delete the play list of which the files are associated with, they also hold the database intact.
You probably accidentally deleted or modified your OMGAUDIO folder on the walkman. I installed the JSymphony program to manage my music, and it automatically fixed the problem.
If you don't want to install JSymphony, the guy who wrote JSymphony wrote an older program which I used to use, NW-E00X_MP3_File_Manager. This comes with an original OMGAUDIO folder, which you can use to replace your own. This should fix any problems (but make a backup of all your audio files on the walkman first, as they may get overwritten in the process).
I had the same problem once with my mp4. I saw that i had put songs on it but they were not their when i tried to play them. what had happened was i had put song on my mp4 that were not formatted for the mp4. So when u plug mp3 back to your pc, see if they song are formatted or mp3 and not anything eal-se. hit me back if you need more info.
The symptoms you described may be due to corruptions in the player's music database (this player maintains an information pool on the music files you download to it). To resolve that, you would need to delete that database and let the player re-create a new one.
To delete the corrupted database, let's do this:
Switch your player to MSC mode
Browse the player in "Windows Explorer", and look for the folder named "System" and/or "Data".
Note: if you can't locate these folders, your Explorer may be configured to "Hide" system files and folders. To change that, please go to "Tools" on the menu list on the Explorer window, then choose "Folder Options". This will display a Window arranged in tabs. Select the "View" tab, find the "Hidden Files and Folders", then choose the "Show Hidden Files and Folders" radio button
Under the "system" or "data" folder on the Sansa E260, look for this file and delete it:
Safely remove your Sansa E260. Then power it on.
Your player will now either display "Rebuilding Library. Please Wait" or "Finalizing Update". Either way, it would re-build the database and hopefully resolve the error your player is encountering.
I hope this helps. I love the Sansa E260!!