1.
After reading your post, I realized that I don't understand what you need or want from the new device clearly. From your previous posts, I got the impression that you don't use Calibre extensively but it seems that you use tag features of Calibre to organize books.
2.
I suggested syncing library across computers because I got the impression that you would like to do that from the following sentences.
Quote:
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I know it won't touche the files on the Reader; that's the problem. I can't download to the Reader at work, and then insert those titles into Calibre when I get home.
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Assuming that you need to sync Calibre
database across computers, I think you can do so by saving databases in one of the Dropbox directories. I don't have any personal experience but it seems that some people do that without any problem.
https://www.mobileread.com/forums/showthread.php?t=38511
3.
About dropbox being 'uploading anywhere', since I am the only person who has access to the uploaded files as long as you don't save files in 'Public' folder, I don't see any problem but you may feel different.
4.
However, given the connection speed and permission to install softwares, using Dropbox may not be very practical for you but it may worth a try. It seems like you have a quite complex situation with lots of constraints and hope you find the right solution.