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I find it strange that you would trust your main library within the dropbox folder. I do hope you also have a backup of it elsewhere.
If it was my library, with all that work classifying things etc as well as being the main storage of my books, I would have my working library on a normal drive. If I wanted to have cloud storage, I would backup to that cloud storage folder.
What happens to files while storing within the cloud storage folder (dropbox, google etc) is not predictable. I consider my library to be too important to not have multiple backups. Yes, a rar backup is rather old school but it is one of the methods I use to get a "snapshot" of the library every few months. I also use FreeFileSync to do regular backups when I make changes. I keep these backups on different drives in case of drive failure.
For files that go to my tablet, I save them from Calibre in the file structure I wish to have on the tablet.
This works well for me and might not for others but I would urge everyone to start making backups. Use separate drives and/or a memory stick.
I guess the effort we tend to put into backups is relative to the importance of the data to us. I just thank goodness for cheap usb drives and memory sticks instead of needing to use those horrid tape backup drives.
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