I confess that I am at a loss.
I am not sure what you are saying about the author formatting. Does calibre believe the book has multiple authors?
What I understand you to be saying about sending is that you sent a book (some books?), calibre thought the send had finished and the books were on the device, but in fact they were not on the device.
Do you have a lot of books on the device? A test using CC with very large libraries (approx 10,000 books) that I have been running with the very kind assistance of DoctorOhh and Sefiriot has exposed some problems that we are fixing. In particular, the timeout you saw can occur when sending many books at one go. Our first fix wasn't good enough. We are preparing now to test a second, more conservative, repair.
Does the error now happen on every send? For sends of books that do not have multiple authors?
The need for a reboot implies that the database manager in Android was confused, or that FCing an app does not release its resources. Either is possible.
What I am going to suggest is unsatisfactory on several levels, but it is the only thing I can think of to do. Sometime this week we intend to release a CC update that contains the large-library changes. It also contains something we should have done ages ago, a debug log that a CC user can send to us. Having that debug log will help enormously when tracing problems like you describe, because we will be able to see the internal sequence of events in CC. The suggestion: we revisit this issue once you have the new version, and assuming that you continue to have a problem.