I have rented a car in Jamaica more then 25 times. It has its pros and cons.
I swore I would never drive in Jamaica for the first few years I visited. Then, I rented a motor scooter, duh, clearly safer in a car. I have been driving ever since.
Pros: if you don't do packages where transport to Negril is included, the cost of 2 people transported each way pays for a car rental nearly for a week.

Easy runs to town square for supplies as often as you like without negotiating with drivers constantly ( the more drivers you deal with, the more likely to have an unpleasant experience at some point).

Cruises up and down the Cliffs, Savlamar, etc at no great expense. Touring thru the countryside....if you do all these things it will way more to hire a driver.
Cons: hassle at airport car rental places on arrival sometimes
Car sits idle when you shouldn't be driving...I need not elaborate
Knowledge that if you must act instinctively in an emergency situation you may go the wrong way.
Never had an accident but I'm sure it would be terrible experience even if nobody got hurt ( I feel safer then I did with many drivers)
Cumbersome chore returning car when leaving Jamaica

Driving on the "other side" is way easier than than you might think.

Stick to name brands at airport. Don't take the collision insurance but be sure your CC covers collision insurance in Jamaica ( many don't)