What would concern me most, if I allowed my Kindle to go online, is this scenario:
- I buy a book from Amazon
- I load it into Calibre (I do this with 100% of my purchases)
- DRM is automatically removed during the process of importing the book into Calibre via the DeDRM plugin
- I side load the book from Calibre onto my Kindle
- Amazon removes the book if my Kindle goes online
I do not know if the item that worries me - item 5 above - actually happens or not. Because I never allow my Kindle to go online for Amazon to get the chance. I do not know what parts of an eBook that DeDRM touches and if Amazon is going to get into a tizzy if they discover such modification and therefore decide to delete my book (now, or in the future after they update Kindle firmware or their cloud servers). I'm not about to test this myself either, because Amazon will also try to update the firmware on my Kindle, and I don't want that either. That firmware update could be the one that automatically deletes DeDRM'ed books!
I doubt I am the only one on these forums that would be annoyed if DeDRM'ed eBooks were removed by Amazon. Again, I don't know that this will happen, because I'm not going to test it. I wouldn't mind reloading books that went missing during a test because I only keep maybe a dozen on the Kindle at a time. But I don't want any firmware update. Amazon could change the functionality of my Kindle in ways that I do not like. Newer is not always better.