> I haven't tried it, but I've looked at it. I think it adds too much complexity. Who decides which files go on the annex and which don't? Doesn't seem like an automated great solution for a scale-able team.

I would put all binary files into git annex (as determined by `file`). This can be done by a commit hook automatically. With another hook that makes sure that `git annex pull` is run when the user checks out code, you'd have a solution that was close enough to automatic for most use cases.

(You'd have to help your users with weird situations from time to time, but that's true of git anyway.)