Every PDQ sailor with outboards has tangled the the hold down line in the prop at least once. If the engines fails to lock and you hit reverse, WHAM, the engine strikes the underside of the bridge deck. Often a portion of the cavitation plate is broken off (harmless, since the engines run deep) and a hole smashed in the deck (I installed a thick sold glass plate years ago--no more problem).
And then there is the swim. It's generally easy. Lift the engine 1/2 way and unwind, though this time the water was only about 60F, I so I wore a dry suit.
This time the eye bolt terminating the lifting tackle broke, but I had a spare in the fastener tray.
No problem. Right back to sailing.