This is a great plan to work towards but I have to inject a few realities here...sorry.
1) Jamaica is expensive, very expensive. The price of gas at the moment is more then in the US and the minimum wage is extremely low, $4500JA a week! For a 5 day work week that is about $10US A DAY! Never mind what it costs to by a car, even a used car...it is more then double, maybe even triple what we pay in North America! Never mind the price of food...that $4500 doesn't go a long way! and that is even if you can find a job.
2) Jobs for Jamaicans are hard to come by with the greatest unemployment rate being amongst the youth, which you fall into that category. What are you planning on doing for a living??
3) You have never visited so I would make a suggestion here that you do. Stay for a short time and then continue to visit, increasing your time on the island each visit. Jamaica Nah Easy!! There will for certain be culture shock, even if you father is Jamaican. It is a "developing" country and they definitely have their own ways, ideas, and culture. You can then visit different regions, or parishes, and decide what suits you.
4) Better yet....Go to Uni first...you will then have a skill, an education to offer and be more likely to be able to get a job. There is no social net to fall back on (meaning no welfare or Government assistance). How are you going to support yourself, pay your rent, pay for food, transportation??? All these things are expensive, no matter what part of the island you live on.
Again, if you have never visited, do this first. Seriously! I have lived and worked in 3 different countries and have the experience of up and moving myself and all my belongings, or most of them, to another country and IT NAH EASY! No matter what country it is. Make a plan. Save lots of money. Go to University first! You will be better off
Now which part of the island to live...again, you need to visit. Each parish, town, and location has it's own vibe/feel and each will have it's own positives and negatives. For the taste of big city life, Kingston, but with that comes crime and violence (like any other big city). The mountains are beautiful, but less jobs (or very few) and more isolation. The west coast is beautiful, great beaches, but again, barely any jobs. The north coast, few bigger cities (MoBay, Ochi) so better chance for a job, but again, what job will you be able to do with little or no experience and you will be competing with a very high number of out of work Jamaicans.
You also need to think about what you are going to do to be legal to work. You say that your father is Jamaican. You need to sort that out. You are not automatically entitled to JA citizenship or the right to live and work on the island. You can't just show up with you US/Canadian/UK passport and say I want to stay cause my father is Jamaican.
Develop a plan, sort some of this out and visit the island a few times while you are doing your research. It will work out better!