Wouldn't it be simpler to run a small background script on your remote that would check periodically whether there the Kindle is up and sync when possible? I am actually doing exactly that. One advantage of this approach is that the syncing can be attempted as soon as the directory content changes, not just on the Kindle network start.
EDIT: to your problem 2: perhaps running in the background (& at the end of the command) could help?
Last edited by janvanmaar; 02-07-2011 at 02:25 PM.
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