iPod Nano 5th Gen Not Updating

[ettore]

I recently purchased an iPod Nano 5th GEN.  I reset it to factory settings, fired up iTunes to "initialise" it, or something to this effect, then used MusicBee to upload some music to it.

I wanted to test if it worked, so I uploaded a 17 track CD to the Nano; everything worked, from what I remember (though, to be completely fair, I "MIGHT" have uploaded those tracks with iTunes the first time).  So, I then uploaded a "running" playlist (about 30 tracks) and got the error below (it happens every time MusicBee tries to, seemingly, write the database).  When you disconnect the iPod, it shows just those initial 17 tracks.  I deleted everything off the iPod and re-uploaded everything, but same issue, except now NOTHING shows up.

I've reset the iPod to factory settings with the newest version of iTunes and tried again, but to no avail.  The files are physically on the iPod (firing up any music player confirms this).  I have tried this on Windows 7 x32 and x64, and tried the resetting using iTunes x32 and x64.  This error started with MusicBee 2.3, so I updated both of my computers today, and the same error occurs on both machines.  I do not get this error with my iPod Shuffle, and I haven't tested my 3rd GEN Nano yet.

Edit: I figured out how to fix it, but it needs iTunes, which is stupid.  Basically, if I fill my iPod up with music (using MusicBee, then get that error), eject it, then upload ONE TRACK with iTunes, then everything shows up; seems like the adding of one track causes iTunes to re-write the database, and it fixes the issue.

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MusicBee v2.4.5404.16303 (Win6.1), 19 Nov 2014 11:00:

System.Data.SQLite.SQLiteException (0x80004005): SQLite error
table item has no column named date_backed_up
   at System.Data.SQLite.SQLite3.Prepare(SQLiteConnection cnn, String strSql, SQLiteStatement previous, UInt32 timeoutMS, String& strRemain)
   at System.Data.SQLite.SQLiteCommand.BuildNextCommand()
   at System.Data.SQLite.SQLiteCommand.GetStatement(Int32 index)
   at System.Data.SQLite.SQLiteDataReader.NextResult()
   at System.Data.SQLite.SQLiteDataReader..ctor(SQLiteCommand cmd, CommandBehavior behave)
   at System.Data.SQLite.SQLiteCommand.ExecuteReader(CommandBehavior behavior)
   at System.Data.SQLite.SQLiteCommand.ExecuteNonQuery()
   at MusicBeeIPod.Parsers.iTunesCDB.SqliteTables.InsertNewTrack(Track track)
   at MusicBeeIPod.Parsers.iTunesCDB.SqliteTables.UpdateTracks(List`1 tracks)
   at MusicBeeIPod.Parsers.iTunesCDB.ITunesCDBRoot.ITunesDB_DatabaseWritten(Object sender, EventArgs e)
   at MusicBeeIPod.Parsers.BaseDatabase.WriteDatabase(BaseDatabaseElement root)
   at MusicBeeIPod.Parsers.MusicDatabase.Save()
   at MusicBeeIPod.IPod.SaveChanges()
   at #=q_1AlolUG_sbmqzyYEkFdCzsgEyw3mn7F82wOP9cezbcgOEWQx_x0UWwyHt7W4T6A.#=qfRrcCmy$GWl6PAt6VdVCXf08m1DErSRi9I3_JoBAT$c=()
   at #=q_1AlolUG_sbmqzyYEkFdCzsgEyw3mn7F82wOP9cezbcgOEWQx_x0UWwyHt7W4T6A.#=qgD0fWhxgZ70VU0f8KSWL5dV38Bzs55RjXONFFn3VpqM=()
   at #=qQoRj6ItoygPd_CN5pMYCQtlVaeqch$tYEyqIe8gRLsw=.#=q$4YUdbW51bR9kUY_KJpzBg==(IList`1 #=qcqEWRNX_VKR91H9tAFh1$Q==, Object #=qLwKfTKVCMtAy2p2mIYaRrWHueGuM_zltFrYcLEn9AR4=)
   at #=qsT9eiAfb8ErN9KwTe$6PSa6ZXnNVSyWdE$xbBk$yj4o=.#=qG2KA9DDD67Igan9u1qGOTEBv8zklWT5OE51k1W$6Jek=(Object #=qtR_wFf59JHSPQlEC88Tceg==)

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[phred]

If you do a search through the forums you'll see that recent versions of iPods are not supported by MusicBee.  I suggest you find iTunes 9.2.1, install it, and re-initialize your Nano.  Then connect it to MB.  No guarantee that it will work, but it's the best I have to offer.  It worked for me a number of years ago.  You can find old versions of iTunes here:  http://www.oldapps.com/itunes.php

[ettore]

Aw, unfortunate .

Oh well, back to Winamp I guess.

[psychoadept]

Have you tried the iPod plugin? 

http://musicbee.wikia.com/wiki/IPod_%26_iPhone_Driver