It looks like it is two independent, unrelated question, but I'll start by answering your first question.
How Long Can You Stay Here?
Well, for a typical visitor to the island, it depends on a number of factors, including where you are arriving from.
After landing in Jamaica, visitors from non-commonwealth countries are usually granted up to six (6) months stay while commonwealth citizens are allowed a up to 12 months, maximum (in total, per year). Note that this may not be all at once.
Note that immigration at the airport will interview you and determine/ advise you accordingly, based on your response to their questions.
Some of the information they require are, for example, where you will stay and proof that you can take care of yourself - and finance your stay.
If you'll require additional time, they have a facility, called the Extension of Stay (EOS) department, where you can apply for extension at the Passport, Immigration and Citizenship Agency prior to the expiration of the time granted initially.
I was told that, at the time of my response here, there is an application fee of 10,000 JMD for the extension of stay application.
Do I Need 'Paperwork' to Stay In Jamaica?
Now, I am interpreting this question to mean, retiring in Jamaica.
If that is the case, yes, you need definitely need 'paperwork' as you call it, to stay here!
In the case where you are retiring in Jamaica, I'd suggest that you apply for permanent residence, aka PR.
Permanent Residence allows you, a foreigner to Jamaica, to live and engage in productive activities while in Jamaica without restrictions on your entry nor gainful employment.
You, the applicant however will be required to do an interview with the Passport, Immigration and Citizenship Agency (PICA) as part of the approval process.
You are already ahead of the game as, to qualify for permanent residence, your application must fall in one of the following four categories:
Employment (3 years and more)
Marriage to a Jamaican
Previous holders of Unconditional Landing status by virtue of marriage to a Jamaican
...and you are applying per 'Residence' (#2 above).
The list of documents that you must present during your application includes,
Evidence of financial status
Certificates and Documents of Business (for Business persons)
Your birth Certificate
Marriage Certificate or Divorce documents where applicable
A Jamaican Medical Certificate
Police Record/ Certificate from your country of residence. Also one from Jamaica if you have been here for over 6 months.
Passport size photographs certified by a JP.
Evidence of asset/property ownership in Jamaica or abroad
A letter indicating why you are applying for permanent residence in Jamaica
Two references letters from acquaintances in Jamaica, and
A non-refundable application fee of 100,000 JMD.
By the way, note that the required letters should be addressed to: The Chief Executive Officer Passport, Immigration and Citizenship Agency 25 Constant Spring Road, Kingston 10, Jamaica, West Indies ( Source: PICA )
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