I also use windows media player and find it works well. When you open WMP you can add you music files to the player but going to "add to library" and then when have all the files you can drag and drop to the mp3 player and sync and all the files should be there. The 'help' section is very good for instructions.
A word of caution...if you are ripping files from a cd that you own it is very easy but make sure you go to the format section and change to 'mp3' files and don't leave as wma files which is usually the default. If you don't do this then your wma music files will not play on your mp3 player and you have to use a program like 'switch' to then change the file format. It is easy to do just when you are ripping.
It is actually easy once you have done it a couple of times. I am just getting ready to put new music on my wife's mp3 player for our trip to the Villages.
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