A Few Things to Try
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Safer picture downloading. Adapt the picture-downloading/file-renaming program to your computer by adding some safety features to make sure you never overwrite a file. A few methods you might find useful are File.exist? (pass it a filename, and it will return true or false) and exit (like if return and Napoleon had a baby—it kills your program right where it stands; this is good for spitting out an error message and then quitting).
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Build your own playlist. For this to work, you need to have some music ripped to your computer in some format. We’ve ripped a hundred or so CDs, and we keep them in directories something like music/genre/artist_and_cd_name/track_number.ogg. (I’m partial to the ogg format, though this would ...