I sail dinghies so am not so familiar with a keel boat with power although I have done some charters and lake Michigan sailing. As I stated in an earlier post I would like to be able to handle this situation with sail. I do agree that once head to wind the motor would be of a big benefit to keep head to wind while reefing the main.
Would you be able to use the engine in reverse to slow boat speed before making a maneuver if you were uncomfortable with speed? I doubt the engine in reverse would overcome your forward momentum but it should slow you down and help add some control ? ? ? ?