The rolling of the directory should be transparent. You can work out which day an excerpt is in by looking at the index but otherwise the appender and tailer dont need to do anything special to make it happen. I suggest having a job in the OS which compresses and/or deletes the files after some time.
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Btw can i quote you on the first paragraph?
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Do you have a twitter handle?
Let me try to put a working example together by tomorrow.