@ssholloway: I have two calibre libraries on an external drive that is attached to my Mac mini running Server. I'm trying to get calibre-server (the calibre content server) automatically started when the Mac mini boots. I have been unsuccessful, but the following plist file starts up calibre-server. (You will need to edit it to agree with whatever parameters you set up in calibre.) (It's similar to the one posted on this thread by abigagli, but which wouldn't work for me. Of course, I changed abigagli's file with appropriate values instead of the square-bracketed stuff.) (Note: The original plist file indents but I'm not sure how to preserve the indenting; I think there's a way to do that but I don't remember how.)
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
<key>KeepAlive</key>
<true/>
<key>Label</key>
<string>local.calibre_server_8080</string>
<key>ProgramArguments</key>
<array>
<string>/Applications/calibre.app/Contents/MacOS/calibre-server</string>
<string>--port=8080</string>
<string>--timeout=10</string>
<string>--username=calibre</string>
<string>--password=egbdfa!</string>
<string>--with-library=/Volumes/WD3TB/Calibre Library</string>
</array>
</dict>
</plist>