Failed copy job deletes all users
So, after Mark's question above, I did some more searching around with much more generic terms (essentially ignoring the loss of the users and just focusing on the fact that the copy job was failing), and came across this thread, this thread, and this thread all of which seem to pretty closely match what I'm experiencing.  This lead me to the observation that, while the views functioned in use, their dependencies were no longer marked, which was what caused the copy job to fail. 

While I'm still a bit curious as to why a failed copy job would wipe out the users in the source database (and why it seems "stuck" in SMO mode), I think this should more or less answer my question.  Thanks everyone.