Can't Sync Window Media Player Playlists

I have developed playlists that use that use some of the same mp3 tracks. For example - I am building a playlist to call coyotes in the woods. I have downloaded mp3 sounds that include howling, silence, wimpers, and barks. In the playlist I ramdomly select tracks from the library and insert them on the playlists. Example - I start with 2 min of silence the another 2 min of silence. Then 30sec of howling, the another 30 sec of howling, them 2 min of silence. Again all the files are seperate and I am just duplicating them in the playlist as I need them. The problem is when I send the playlist to the sync portion of Windows Media Player. The player automatically throws out all the duplicate files and leaves me with an altered playlist which won't work for my needs. Is there a way to correct this or to manually drop audio files from my library directly into my device. This works on my Dell DJ but that is different software. I don't want to use my Dell DJ in the woods for fear it will get damaged. I bought two different cheap mp3 players that sync with Windows Media Player and both had the same results so I believe Windows Media Player is the problem not the cheap mp3 players.

Thanks in advance for anyones help.

Hello, if you are getting the problem in the Sync of Windows Media Player Playlist then you will get all of the solution for your problem from the Microsoft for that and you just need to visit to the link below:

Windows Media Player sync