I have a similar idea, and I'm sure it's feasible.
At least I THINK it's a smilar idea:
I have files that I create regularly with Calibre in MOBI format. I have to copy them from my laptop to my Kindle using a USB cable.
I don't want to use a USB cable, I want to copy them wirelessly.
But I can grab files from lots of places, such as Project Gutenberg, and they copy to my Kindle with no effort and at no charge.
So, in theory, all I would have to do is set up a similar environment and I would be able to copy my files to my Kindle as easily as I can copy Project Gutenberg files to my Kindle.
The only problem is, I don't know how to do that. I think it's easy, though.
Anyone know exactly how to set up a file server similar enough to allow MOBI files to be copied to a Kindle 2 wirelessly?
Or is there a problem I'm not aware of?
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