How do I copy files between separate iTunes accounts/libraries?

First, create a temporary folder somewhere on your computer’s hard drive. For example, C:/iTunesTransfer/ will work fine. 
Next, in iTunes account #1, find the playlist that you’d like to copy into iTunes account #2. Select it, and choose Edit—>Select All from the menu bar. Then, simply drag these entires out of the iTunes window and into a Windows Explorer window of your C:/iTunesTransfer/ directory. This will place copies of the files into that directory.

Then, log in to account #2 and open iTunes. Locate the C:/iTunesTransfer/ directory, and drag the files from Windows Explorer straight into the iTunes window. This will place copies of the files in account #2’s iTunes Library.  If you’d like to instantly create a playlist of these files, then instead of dragging to the main iTunes window, drag directly into the “Source

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