outside in doesn't actually work for overhangs. think about it.
You have to build out gradually, so starting on an unsupported area won't work.

And don't think it won't do that, it will.

I did something recently that was a shaft with a hole at the top. Instead of bridging the gap and gradually creating the hole via the bridging - which is waht i thought it would do. It actually wanted to print the outline of the hole first - in thin air.