I'm an expat from Jamaica, (Jamaican born) currently in India. I just though I'd check out what people have to say or ask about Jamaica. Having seen your post I'll be glad to answer your questions to the best of my knowledge. :-)
As I'm Jamaican, life for the expat (costs) will be slightly different from cost of living for the locals like myself. (But I now have expat blood in me, lol).
Accommodation - For an expat I assume you'd want to live in a nice and safe neighbourhood where other expats tend to live, costs for furnished housing 2 bedrooms is at least $1500us, 3 bedrooms upwards you're looking at around $2500us per month upwards. Most times water and electricity and maintenance are included, A/C and water heater are usually included for fully-furnished apartments catering to expats. Back in 2008 I paid US$1000 p/m for a 2br furnished with a/c. Water, electricity and cable/internet was additional cost. This was in Long Mountain Country Club, a nice and very safe with high security neighbourhood up in the hills, above Beverley Hills in St. Andrew.
We now have a good public (bus) transportation system called JUTC (govt run), very good compared to some of the countries I've been to, like here in India for example, Mexico, Kenya, I opted for taxi instead. But JUTC is expat standard, easy access and fairly smooth system. The transport centre is in Half-Way-Tree, roughly 4km from New Kingston. The fare was recently increased this year to JMD$80 (Jamaican dollars) per ride for adults. This is within the corporate area, Kingston and St. Andrew, where you'll be seeking accommodation. We don't have any tubes, sorry...wish we had. We also have some good and reliable (on-call) taxi services. I particularly use Ontime Taxi company whenever I don't feel like taking the bus, very reliable, always on time as their name suggests. Let's see, for between up 4km (not sure) cost is JMD$ 350. I've paid up to $400 for travel within 8km my estimate. For me, from Drumblair community near Barbican to New Kingston (business zone) JMD$350. From Drumblair to Carib 5 Cinemas for movie, which is in Cross Roads, JMD$ 400.
Food - being an expat myself, I want to eat well, the exotic fruits, treats, etc. I have an expat friend who was living in Jamaica at the time back in 2007 and his grocery bill for a month for a family with two kids was an estimated JMD $100,000! (included lots of fruits and vegetables) That's what he said, I was shocked. But for me, even recently I was in Jamaica and the cost is roughly $15,000 per week if you cook (meatkind) everyday. I'm a family with 1 almost 2 years old boy, so costs for diaper and baby cereal/formula included.
Medical insurance - hmmm...can't say. Usually people get this through their companies, as a part of package benefits. You can check out Sagicor Insurance, Guardian Life Insurance, those are the two popular ones I know. Personally I don't have medical insurance since I started travelling as an expat.
Education - what age? For public schools, government 'says'
education is free, but parents still paying high fees such as auxillary/admin fees. My little sister-in-law just started 6th form/grade 12 and had/has to pay around JMD25,000 for the year (if I heard right). Private schools - like for those that expat kids go to, will definitely cost you. Not aware of the annual tuition. Check out Hillel Academy, Campion College. The 'bright/smart' students who score top/very high marks on their 6th grade examinations go to Campion College. Not sure if you can 'buy your way' in at that level, so expat kids would have had to be going to a primary(govt) / private (prep)school before going there (I think). Hillel is more for expats, upper class/rich kids in a private school setting. For daycare, I sent my little one just earlier this year while I was in Ja, daycare costs between JMD$20,000 to JMD$25,000 per month. They keep them from as early as 7am to 7pm weekdays. Some provide 3 meals per day. With some no specific time/month as to when to register.
Electricity - if you're away from home in the days and have basic appliances and electronics such as fridge, tv, a/c, washing machine, computer/laptop it can range from $6000 to $12,000. I'm not home (Ja) to check the cost per kwh on the bill, but my dad's bill is $12,000 tops, he's always home on the computer (3 persons in that household), my sister's bill is $3000 tops, she's away at work during the days and mostly uses her laptop at nights, no a/c or washing machine/dryer.
Internet/Cable/Telephone - I use FLOW, a fairly new company in Jamaica. For Internet and Cable $4600 per month. It can be more depending on the number of channels you subscribe to. I use their prepaid landline phone, only buy credit and top up. I also have a mobile with DIGICEL, there is a 25% govt tax on mobile, so a $1000 credit (airtime/recharge) will cost $1250. $10 per/min digi to digi calls, for oversees calls around $18 per min, per second billing, plus there are off peak rates. I find Digicel to be very reasonable in comparison to some mobile companies that I've had to subscribe with whenever I'm in a foreign country.
Gas/Petrol - the last time I was in Jamaica (earlier this year) around $95 average for premium 90 unleaded, and $85 per litre, average for unleaded 87/now E10 gas.
Restaurants - there are so many nice ones, like Rib Cage, TGIF, Cuddy's Bar & Grill, Gloria's in Port Royal, decent bill (meal and drink) $2500-$4000 for two persons. Can be more depending.
Coffee/beer - Jamaicans are not necessarily coffee fans when it comes to hanging out, even though we have the great blue mountain coffee, however we're more beer, alcoholic beverages fans... In the clubs/bar & grill joint you'll find heineken going for $250-$300, Red Stripe slightly cheaper. In the supermarket definitely cheaper as with any other country. (My husband complains about India Delhi, Rs400-500 for beer in the clubs, that's like around $700-$900 equivalent to Jamaica.)That's for their Kingfisher beer. Never seen Heineken there :-(
Cinema - I go to Carib 5 in Cross Roads, on par with some other cinemas I've been to in other countries. Another popular option for expats is Carib/Palace Amusement owed Cineplex inside the Souvereign Centre Mall. Check out their website. I paid $650 per person just this year. They have 2 for 1 specials where the movies are almost always sold out. Food there is expensive, 2 large pop corns and 2 sodas, around $1000. But, the same for other cinemas in some countries. No searching of bags and confiscating of chocolate inside your bags like they do in cinemas here in India. Gosh. In Jamaica, as long as your outside food is not visible to the security like your KFC meal or Burger King meal, then it's fine. (So far).
Wow this is a long reply...hmmm
I think I've chatted enough :-) Hope the questions have been answered to your liking.