Jellyfish,
Welcome to the Board. I founded and registered Negril.com back in the 1990's so I have a little experience in this area. You really dont need an immigration attorney as it sounds like you have a good take on things.
Being a member of the Commonwealth makes it a bit easier. In February, you will first need to register your company and get a TRN for you and the company. Then you can apply for a self employed work permit with all the necessary forms. You will need to apply for three years before you can apply for residency with work privileges.
That being said, to be granted a permit, it matters what your business does and what you "bring to the table". Unemployment is rather high here, so if you are not hiring anyone that is a negative. You say your clients are based abroad, so although you wouldnt be taking away a job, you are also not servicing any businesses/people here. This seems like another negative. If your business makes alot of money and you are paying the income taxes here, that is definitely a plus.
Good luck! Kingston is a fun city.
