Yep, Experienced all of the above...... (thankfully in open water)
One time in the dim & distant the bloke on the Yacht I was towing (at about 6 knots) didn't notice the gentle gust of wind, and went from a good 20M behind to on top of us in a matter of seconds - catching my transom (near miss - a foot to the right & he'd have been on top off us) & spinning me round I was dragged backwards by his momentum until his crew un- cleated me. (by this point we were both perched on the bow of the rib to try & keep the transom as far up as possible & cwondering why we didn't step aboard the yacht on it's way past!)
I now have a remote release rope / snap shackle arrangement on my tow bridle!
Slight tangent to the thread, but illustrates the "boat behind" point nicely. - and never assume anything!