So is your boat in Florida or Michigan?
If you want to sail your boat from Michigan to the Caribean, you will probably have to beef it up all along the way! The question is ... why do you want to sail the MacGregor there? With the expense and time it will take to beef it up, you could probably invest the money in something more comfortable. The money you spent to purchase the boat is probably insignificant to the cost of beefing up the components.
I read an article about a guy who sailed a windsurfer from Venezuela to Florida, island hopping all the way so he never spent more than 24 hours on the water at a time. But he was going largely with the prevailing winds and waves. The route you intend to take is called the 'thorny road' if I'm not mistaken because it is against the wind and waves, making it a bumpy ride all the way. Franklin suggests an oceanic route for good reason, but as he outlines, the boat preparation is daunting to say the least. If you are going to follow the thorny road, I suppose it would be possible to keep your jaunts to a minimum and it would be possible to watch your weather windows carefully. With unlimited time and plenty of money in your bank account, you could replace components as needed, always replacing with the appropriate materials for the job. If you have plenty of luck, nothing will fail that causes you to go for a swim! I'd bet that you would replace virtually all the components on the boat on your way from Michigan to Florida anyway! When you see the hull flexing, build in some reinforcements as needed along the way when you are in port! When you notice the instability of your boat in the waves, you may think of the right solutions. With the right amount of trial and error, a great deal of luck, and a good feel for the way to improve your boat, you just may make it as long as your money lasts!
Good Luck!