planning for the future

at my age, 48, most people these days have at least a nebulous idea of what they want to do for their retirement - if they get to retire at any rate. They've been to meetings on investment plans, GICs, RRSPs, time shares, pension plans and payouts, tax shelters etc. Up to this point I have kind of just ignored them and thought - I've got lots of time. I was possible planning to go back to school and do my Master's, maybe at the University of the South Pacific and had started to investigate what coursework was available on what island. But nothing really specific.

Now. I am motivated. My retirement destination is Jamaica. And I have been investigating all the things that I will need to plan/arrange/investigate/prepare for in order to make my dream come true. I figure a cool quarter million should look after me for at least 20 years and I'm not likely to last much past that. If anyone out there has dependable resources that apply to my list please leave me a comment.

1. What is required to be allowed to live in Jamaica.
2. What is required to maintain Canadian citizenship.
3. Can I have dual Jacanadian citizenship or is that even a good idea
4. Tax laws for above.
5. Do I need a work Visa for Jamaica?
6. What is the best real estate company to deal with when purchasing internationally.
7. Investigate health care alternatives.
8. Shipping costs for a PUP and a car, Canada to Jamaica.
9. Expenses, what will I need to live on? Power, Water, Gas, property taxes, beer.
10. How much interest will I be earning on my lump sum investment?
11. Best way to invest lump sum?
12. Onshore or off shore account?
13. Boat and motor, mooring costs?
14. Annual travel budget for hurricane season ;)