yes, you can, the command line server automatically detects changes to the database.
The calibre server has no concept of files or directories. It is fully virtual. It just uses names, so
http://localhost:8080/browse
in which case trailing slashes are pointless, they just mean more to type. In some cases it will simulate filenames so that the browser can download a file, but that's about it. I suggest turning off your canonicalization for the content server