Looking at the comments here, it appears people are trying to do too much, too soon, which inevitably backfires. The key is to put OC in a sandbox (don't give access to your real accounts, it must have ints own separate non-admin accounts for everything only "invite" with limited access as you would a contractor) and generally treat it as a new employee during a trial period. You'll be surprised by how effective it can be if you pace yourself.

As for "you can easily do X,Y,Z with a cron job" we tech people often underestimate what hiding the complexity could do for UX.

"For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem." -- top comment on "Show HN, Dropbox (2007)