On the winch, if the wing drops, release immediately, you don't have time to consider your options. There's a good chance you can't do it fast enough, and it's going to hurt.
The wing runner isn't going to do a lot of running, if they start you from a balanced position, (which might be slightly different than wings level), and your control inputs are neutral, you will have aileron control and flying speed very quickly after the "All Out" calls.