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OK,
I haven't tried this yet....
But my thought is...
1. Put all your ebooks on Dropbox.
2. create a script that crawls your ebook folders, gets all the info and builds a .mobi ebook and puts it into drop box.
3. On kindle go to your browser and input the URL for the .prc that is a list of all your ebooks. That will download it. Then you can browse through the file, also search and it will have D/l links for each file in drop box.
This is very similar to what feedbooks and MR do. You could probably even get some Calibre action going and use it's database so that the index book you create has summaries etc in it.
Perhaps someday when I am bored I will give it a whack.
BOb
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