V-Man,
You have many options available to you.
Can I automate the process of copying the tracks of a playlist to the root directory of the device, at the same time naming them based on their playlist position? The USB player can only play files in the root dir in alphabetical order.
If your player handles nested folders, try right clicking on the player's drive letter and choose synchronize (you can also click on the little Portable icon in the task bar). When you are in the synchronization dialogue, you can select Playlists and they will be created on your player under a subfolder called Playlists. If your files must be at root level, either right-click on files and 'Send-to' your drive or drag and drop files either on the action window or on the player drive letter.
In regards to the alphabetical playback, one option will be after your files are named based on playlist position, right click on the drive letter and select the option Select Name/Filename field and select 'FileName'. With this option selected, files will appear on your player named by the filename on MC which will handle the alphabetical playback requirement of your player. If your player supports nested folders then you should be ok.
When you are ready to transfer files if you click on the root level, you will see information about available space and if you click on 'Options' you will see the ability to do on the fly conversion of files. If you use synchronization, you will also see available space information and 'Options' for conversion. As you change conversion options, the available space will estimate the available space and display this to you.
Steve