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From what I've researched, there are at least two issues that can cause problems. One is the fact that Calibre is not multi-user. If more than one thing tries to access the library at the same time, you are potentially in for corruption. It would be nice if in the future Calibre could switch to using an actual relational database backend.
The second is that Calibre uses "special" characters in it's file naming convention. You'll see parenthesis in there, spaces, dashes, etc. While all these are not truly "special characters" for individual OS'es in the strictest of meaning, they are "problematic characters" when viewed as a whole. Maybe in some future version, Calibre would switch to only using alphanumerics and an underscore. That should be safe everywhere.
But to make a change like this, either moving to an actual RDBMS or changing file naming conventions, you have the headaches of backwards compatibility, conversion of existing libraries from old format to new format, etc. This would definitely be a major version change, from the current 3.xx to 4.xx, with ample warning that a "non-reversible library conversion" would be part of the upgrade. Of course, running a relational database over something like DropBox, would be, shall we say, very much a "programming challenge"!!! Calibre is a local server. It's way too complex/sophisticated to be DropBox-able IMHO, despite many folks evidently trying to force it to do exactly that. DropBox and other cloud drives are for files, not applications. There are cloud based applications as well, but that's not something your everyday Joe who just wants to read eBooks is going to be able to implement/configure.
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