In 1988 when I first purchased my 201, I flew from New Orleans to Cozumel with 4 adults, during the evening hours. Despite strong tail winds, we landed far short of FAA mandatory reserves of fuel. On the return flight, we decided NOT to do this again and flew over Cuban airpace through Florida and back home. I had only the standard 64 gallons of gas on board
To this date and after 27 years of flying, I think the Gulf of Mexico flight was the worse decision of any flight I have ever made. And I speak of this frequently knowing that there were no options mid flight. When flying and driving, I always try to leave myself alternatives. Sometimes thats not possible for only for a short part of a trip. Flying over the Gulf leaves you no options, no second guessing, and no immediate availablity of Help if needed.
So if you want my two cents, just count the number of NO's in this response compared to the number of Yes's.. Pretty obvious.