I'm starting to get a handle on file user management. I still have some questions:

Does keeping everything writable pose a security risk? (all my projects are on VPS or dedicated servers)

Keeping up with dirs/files created by Drupal can be accomplished with a recursive chmod and svn add. What about files that Drupal deletes? I.E. a node with an attached file is deleted or imagecache settings are changed flushing the dir. The files should be removed from the repo as well. Imagecache dirs could be set to svn ignore since the files are created on the fly. But not all modules are that obvious.

I guess what I asking is: Does maintaining the files directory under version control over time with an active project require lots of manual tweaking and upkeep?