I need to copy a file to 300 compact flash cards at work, to speed up the process a little, I'd like to do about 5 to 10 at a time, by hooking up 5 to 10 USB Compact Flash card readers to a PC.

What would be the best way to do the copying?
Is there a way to do it automatically, that a file/image gets copied as soon as I insert a CF? That way I'd need less readers (and typinG).