CAYMAN ISLANDS - Fastrack to FIRE

[FIREupDOOON]

HI EVERYONE - I HAD ORIGINALLY POSTED THIS ON THE AUSTRALIAN TAXES FORUM, BUT WANTED TO SHARE HERE TOO TO CAST THE NET AS WIDE AS POSSIBLE. SOME OF MY QUESTIONS ARE AUSTRALIAN TAX FOCUSSED, BUT IM MORE INTERESTED IN HEARING FROM ANYONE WITH EXPERIENCE LIVING/WORKING IN THE CAYMANS!

THANKS

..................
Hi everyone

As the subject title suggests, I am (most likely) moving to the Cayman Islands.

I wanted to reach out to the infinite wisdom of the MMM forum to hear people’s thoughts, ideas, recommendations (?), criticisms (?), and tax issues of making the move.

A little about me:

- married no kids
- age 29 (me) 27 (wife)
- live in Australia

- assets (all jointly owned):
-—home ($800K)
-—VTS ($65K)
-—superannuation ($70K))
—-cash ($10K)

Liabilities:
—-home loan (~$500K)
—-HECS ($30K)

Income:
We both work fairly high paying jobs which bring in a total of $240K per year.
We save about $9300 per month (this includes compulsory superannuation contributions).

WHY THE CAYMANS?
That’s easy:
- live on a tropical paradise island
- work less
- earn (a lot) more

I’ve done the sums and, provided I successfully migrate our tax residences to the Caymans, we should (at a minimum) be saving an extra $4000 per month (AUD).

The above number is based on a couple of assumptions:
- our living expenses increase DRAMATICALLY to about $9000(AUD) per month. This includes a mortgage in Aus, rent in Caymans and everything else in Caymans.
- my wife doesn’t earn a cent. Although this is not realistic, the nature of our income over there will have me as the primary earner. There are job prospects for her over in the Caymans, but (at least right now) they’re less certain so I’m discounting them. The good thing about discounting her salary now is that anything she does earn will be complete and utter gravy - straight to the bank.

Based on our current stash and our projected incomes, a move to the Caymans fasttracks our FIRE date by 3 (or so) years. If all goes to plan, we could be retired in 4 (maybe 5) years from when we move.

I HAVE QUESTIONS!!

- has any one here done the same? Help me out!

- does anyone here LIVE on Cayman? Would love to hear from you

- tips for ensuring my residency is migrated over from naughty taxing Australia to nice non-taxing Caymans?

- I plan on renting out my home. What should I think about? I’ve assumed I can’t still treat it as my “home” for CGT purposes (I know there are rules for doing so even though you don’t live there and rent it out for 6 years....but I’m fairly sure that wouldn’t play nicely with the whole “residency” thing.

- once I’m there - WHERE should I invest? I currently use SelfWealth to invest. I’m assuming the best bet for me would be to invest in something local?

- IF I do come back to Australia after hitting FIRE, what happens with my offshore investments? This sounds like a tricky question that I’ll get professional advice on, but still - if anyone has experience doin it I’d love to hear!

Thanks for your time!

[jim555]

I saw a show on the Caymans.  Supermarket prices are insane.  A couple bought 3 items and it was $50.

[FIREupDOOON]

Hi Jim555

Yes, the cost of living does seem to be outrageous.  If it weren’t for the even sillier wages, there’s no way you could even consider it!

[o2bfree]

I did a dive trip on Grand Cayman back in the early 1990s. Food prices were insane. As I recall, a crappy medium pizza from Pizza Hut was $21. Also, the island of Grand Cayman is very flat. The highest point is 18 m (59 ft). I got nervous when thunderstorms moved through. It'd be really frightening in a bigger storm or a hurricane.

[FIREupDOOON]

Hi O2bfree

Cost of living is the main point of contention for me. Although, Australia is a relatively expensive place to live so the cost comparison isn’t as drastic (especially in relation to food/alcohol).

Flooding and hurricanes are also an issue. I think there was some flooding in the past couple of years. Nothing catastrophic though.

What was the diving experience like?

[o2bfree]

Hi O2bfree

Cost of living is the main point of contention for me. Although, Australia is a relatively expensive place to live so the cost comparison isn’t as drastic (especially in relation to food/alcohol).

Flooding and hurricanes are also an issue. I think there was some flooding in the past couple of years. Nothing catastrophic though.

What was the diving experience like?

The diving was great! Great visibility, nice reefs and walls, and really warm water. People were friendly enough too. I remember that women dressed very professionally in town: long-sleeved blouses, long, pleated skirts, and high heels, even in the heat. I felt a little like white trash wandering around in shorts and a tank top. Things may be different there now, of course.

[partgypsy]

here is an article that talks about various ways you can be a (tax paying) resident of Cayman islands
https://www.ogier.com/publications/securing-cayman-islands-residency-by-proof-of-independent-means-or-by-way-of-direct

Residency Certificate for Persons of Independent Means
An individual who is able to demonstrate that he has a continuous source of annual income of CI$120,000 (US$146,341.46) without the need to work in the Islands or that he has an account with a Cayman Islands Monetary Authority-regulated and locally licensed institution and maintains a minimum deposit in the account of at least CI$400,000 in assets and that he has invested at least CI$1,000,000 (US$1,200,000) in Grand Cayman of which at least CI$500,000 (US$610,000) must be in developed real estate, may apply to the Chief Immigration Officer for a Residency Certificate for Persons of Independent Means.

Certificate of Direct Investment
A person who makes, or proposes to make, an investment of at least one million dollars in an employment generating business – either existing or a new venture - and in which he plans to exercise substantial management control, may apply for a Certificate of Direct Investment.The words ‘employment generating business’ mean a business in which at least thirty per cent of the total number of employees are Caymanian unless it can be shown that overriding circumstances dictate a lower percentage.

Residency Certificate (Substantial Business Presence)
This is a long-term residence category for persons who invest in, or who are employed in a senior management capacity, within an approved category of business. The category is open to persons already resident in the Cayman Islands and persons wishing to become resident. The words ‘employment generating business’ mean a business in which at least thirty per cent of the total number of employees are Caymanian unless it can be shown that overriding circumstances dictate a lower percentage.

Residency Certificate (Substantial Business Presence)
This is a long-term residence category for persons who invest in, or who are employed in a senior management capacity, within an approved category of business. The category is open to persons already resident in the Cayman Islands and persons wishing to become resident.

so it looks like you either need a) to be hired for a job in Cayman islands, b) a lot of money 1million+, or c) have a business where you hire caymanians as employees. this is a brief look through though. 

[MrThatsDifferent]

So, you’re doing this just to avoid or reduce taxes? That’s a pretty bold move if that’s your only goal. I’m presuming you have a job you can do from anywhere in the world? Have you looked at other options? What about Malaysia? Ideally, if you’re moving, you’d want a combination of tax savings and reduction of living expenses, not an increase.  How long would you need to live there to reach FIRE? Are you both  prepared for it and sure you won’t be bored?

I also don’t understand how you make so much and can save so much but your actual savings is quite low? Have you been funneling all your money into the house? Why do you need an $800k house in Brisbane if it’s the 2 of you? That place would be a mansion as you can easily get a 2 bedroom for $500k.

What’s your plan when you get all the money that you want for FIRE? You’re quite young and would have a long time to get to your Suoer. Look through the Australian investment forum and find BigChris, i’d Private message him. He’s a genius at this and has made a shit ton early and currently lives in the Netherlands. He might be able to give you ideas on what you can do to stay in Australia but manage your situation better?

[flipboard]

If your absolute savings rate increases, no reason why not. Comparing COL is useless if you don't take into account income and taxes. (Everyone I know who moves to a certain specific HCOL country ends up saving way more money in absolute terms because their salary is either the same as in other HCOL areas but with lower taxes/expenses, or because their salary went up a lot and taxes down relative to their previous MCOL/LCOL area).

I'd be more wary of the personal difficulties: moving countries isn't always that easy, changing lifestyle's likewise - long flight times to see family can also be hard. Having one partner stop work can be a difficult transition. That's where I'd recommend thinking and evaluating carefuly.

[jim555]

No income tax, no cap gains tax.  Australia only taxes its residents, once you leave they leave you alone, unlike the US.  I can see why you would want to go there.

[FIREupDOOON]

here is an article that talks about various ways you can be a (tax paying) resident of Cayman islands
https://www.ogier.com/publications/securing-cayman-islands-residency-by-proof-of-independent-means-or-by-way-of-direct

Residency Certificate for Persons of Independent Means
An individual who is able to demonstrate that he has a continuous source of annual income of CI$120,000 (US$146,341.46) without the need to work in the Islands or that he has an account with a Cayman Islands Monetary Authority-regulated and locally licensed institution and maintains a minimum deposit in the account of at least CI$400,000 in assets and that he has invested at least CI$1,000,000 (US$1,200,000) in Grand Cayman of which at least CI$500,000 (US$610,000) must be in developed real estate, may apply to the Chief Immigration Officer for a Residency Certificate for Persons of Independent Means.

Certificate of Direct Investment
A person who makes, or proposes to make, an investment of at least one million dollars in an employment generating business – either existing or a new venture - and in which he plans to exercise substantial management control, may apply for a Certificate of Direct Investment.The words ‘employment generating business’ mean a business in which at least thirty per cent of the total number of employees are Caymanian unless it can be shown that overriding circumstances dictate a lower percentage.

Residency Certificate (Substantial Business Presence)
This is a long-term residence category for persons who invest in, or who are employed in a senior management capacity, within an approved category of business. The category is open to persons already resident in the Cayman Islands and persons wishing to become resident. The words ‘employment generating business’ mean a business in which at least thirty per cent of the total number of employees are Caymanian unless it can be shown that overriding circumstances dictate a lower percentage.

Residency Certificate (Substantial Business Presence)
This is a long-term residence category for persons who invest in, or who are employed in a senior management capacity, within an approved category of business. The category is open to persons already resident in the Cayman Islands and persons wishing to become resident.

so it looks like you either need a) to be hired for a job in Cayman islands, b) a lot of money 1million+, or c) have a business where you hire caymanians as employees. this is a brief look through though.

Thanks partygypsy

You’re right - those are really the options for becoming a Cayman permanent resident. I would be granted a working visa and residency when I get there (through my employer). However, because there is no income tax on CI (and Australia has no treaty with CI) there is still a risk of my residency not migrating. It can depend on silly things like how many days I’m in Aus during a financial year and goes to my intention - the tax office will ask - “was it his intention to not leave Aus permanently (or at least for the foreseeable future)?”  - if not then I might still be a (tax) resident of Aus (and a resident of the CI at the same time).

[FIREupDOOON]

So, you’re doing this just to avoid or reduce taxes? That’s a pretty bold move if that’s your only goal. I’m presuming you have a job you can do from anywhere in the world? Have you looked at other options? What about Malaysia? Ideally, if you’re moving, you’d want a combination of tax savings and reduction of living expenses, not an increase.  How long would you need to live there to reach FIRE? Are you both  prepared for it and sure you won’t be bored?

I also don’t understand how you make so much and can save so much but your actual savings is quite low? Have you been funneling all your money into the house? Why do you need an $800k house in Brisbane if it’s the 2 of you? That place would be a mansion as you can easily get a 2 bedroom for $500k.

What’s your plan when you get all the money that you want for FIRE? You’re quite young and would have a long time to get to your Suoer. Look through the Australian investment forum and find BigChris, i’d Private message him. He’s a genius at this and has made a shit ton early and currently lives in the Netherlands. He might be able to give you ideas on what you can do to stay in Australia but manage your situation better?

Hi MrThatsDifferent

Thanks for the comment. I’ll try to touch on each of your questions.

1. I’m not considering the move just to avoid taxes. There’s quite a few things that draw me there. Firstly: lifestyle and work life balance.  Everyone I’ve spoken to tells me the lifestyle is relaxed and there is a legitimate work-life-balance (something that is missing from my life right now).

Secondly: tropical paradise/great weather. Yes, Australia has amazing weather for which I am grateful, but I think we can all agree there is a difference between living in a inland city and effectively living right on the beach. It’ll be like living on the Gold Coast except less bogans (there might be a Cayman Island equivalent of “bogan” - I’ll let you know)

Thirdly: $$. I can earn a lot more money. Quickly. Even with my COL skyrocketting, the increased wages and lack of taxes more than makes up for the increase. To put it in perspective, I expect to be able to earn another $4K(AUD) a month from the moment I set down. This number will only increase the longer I stay as my pay increases. For me to save an extra $4K a month here in Aus would mean a tremendous payrise for my wife and I overnight (not likely). We may eventually earn that money here - but it’ll take 4-5 years to get there.

2. My job is not something I can do anywhere. I’m limited to certain countries. It just so happens that, in Australia, I get paid less than most other countries. Other options are London or NY for large $$. Could probably earn the same amount - and the cost of living would be less - BUT I’ve shied away from those places because:

- ZERO work life balance. To earn that money id effectively have to sell my soul. Even more than I do now. Would never see my wife. If I have kids, wouldn’t know their names. This is probably a bit of an overstatement, but you get my drag.

- Weather/lifestyle -  I think we can all agree London weather might be a bit of a downer after a while. NY, I’ve never been to. My main issue with both of these places is the super mega metropolis atmosphere. Coming from Brisbane, I’m not used to it. Living at the beach does have a nice ring to it.

- I’d be taxed on my income in most other places. This makes my additional pay go further. Yes the VOL in CI is very silly, but I’m more than compensated to combat it.

3.  How long will we be there? Are we prepared? Will we get bored? 

- probably 4 years (depends on how much my wife earns, to be honest). After that I expect we will move again most likely the UK or US to visit family and explore.

- prepared? We’ve moved cities before. My wife has moved countries before. So moving around is not foreign to us. You’re right though, there is A LOT to consider. My post below may have made it sound like we are focussed solely on the money - but that’s not the case - we’re keen for the change and looking forward to the adventure.

- bored? I don’t think so. I’ve built in to our budgets plenty of space for travel and fun. My work should actually be pretty exciting too!

4. Savings rate. I’m not sure I understand the question. For the past 9 months or so we have saved $9300 per month. This is made up of about $1700 in superannuation (compulsory retirement savings which come out of your pre-tax salary) and the rest in deposits in to our index funds. The rest of our income goes to our mortgage (minimum repayment) and the rest is on living/bills etc.

5. House. Well, I’ve been lucky in that I bought a few years ago and house prices have gone up. I also put in a LOT of my own time and sweat to improve the house. $800k is the bank value at the moment. If I want a HOUSE that isn’t complete bollocks in a nice-ish area you will need to spend more than $500K. An apartment is a different story. The house will be rented when we leave - earning a nice little income. It won’t cover the costs but it’ll be something.

If we did come back to Aus, we would 100% downsize into something smaller and in a walkable area. But right now, the house is my best asset - it will allow me to downsize mortgage free (or close to it) if I decide to come back to Aus.

6. Plan after FIRE. I don’t intend on completely stopping work. I’d probably take a year or two off then find something part time and enjoyable. Tutoring maybe?

7. I’m not sure there is much I can do to manage my income here better.   I’m  trying to live a moustachian lifestyle. Spend little. Save lots. Index funds. There are definitely funky things I can do with my superannuation (this can be complex and expensive and usually only works when you have bulk coin in your super). But I’ll touch base with your suggestion in any event - if anything his life does sound interesting!

Hopefully I answered everything.

Cheers

[FIREupDOOON]

If your absolute savings rate increases, no reason why not. Comparing COL is useless if you don't take into account income and taxes. (Everyone I know who moves to a certain specific HCOL country ends up saving way more money in absolute terms because their salary is either the same as in other HCOL areas but with lower taxes/expenses, or because their salary went up a lot and taxes down relative to their previous MCOL/LCOL area).

I'd be more wary of the personal difficulties: moving countries isn't always that easy, changing lifestyle's likewise - long flight times to see family can also be hard. Having one partner stop work can be a difficult transition. That's where I'd recommend thinking and evaluating carefuly.

Thanks Flipboard

Agree - that’s going to be the hardest part for sure. The way I look at it though is that this move will give me the freedoms I want quicker! So I can spend as much time with family as I want once I’ve FIRED.

[ericrugiero]

5. House. Well, I’ve been lucky in that I bought a few years ago and house prices have gone up. I also put in a LOT of my own time and sweat to improve the house. $800k is the bank value at the moment. If I want a HOUSE that isn’t complete bollocks in a nice-ish area you will need to spend more than $500K. An apartment is a different story. The house will be rented when we leave - earning a nice little income. It won’t cover the costs but it’ll be something.

If we did come back to Aus, we would 100% downsize into something smaller and in a walkable area. But right now, the house is my best asset - it will allow me to downsize mortgage free (or close to it) if I decide to come back to Aus.

I would consider selling the house and investing the equity.  You aren't planning to move back to the same house and it isn't covering the costs anyway so why not sell?  You would avoid the headaches from doing a long term rental. 

It seems like a brave move but one that could make sense from a money and life enjoyment standpoint.  Before I pulled the trigger, I would want to know for sure what the tax implications are for Australia trying to tax you while you are out of the country or if you try to move back.  My plan would be to talk to a local accountant, tax preparer, etc. 

[Gremlin]

5. House. Well, I’ve been lucky in that I bought a few years ago and house prices have gone up. I also put in a LOT of my own time and sweat to improve the house. $800k is the bank value at the moment. If I want a HOUSE that isn’t complete bollocks in a nice-ish area you will need to spend more than $500K. An apartment is a different story. The house will be rented when we leave - earning a nice little income. It won’t cover the costs but it’ll be something.

If we did come back to Aus, we would 100% downsize into something smaller and in a walkable area. But right now, the house is my best asset - it will allow me to downsize mortgage free (or close to it) if I decide to come back to Aus.

The bolded bit will almost certainly have consequences if you are trying to extricate yourself from being an Australian taxpayer.  You should definitely get yourself proper tax advice as this sort of thing is easy to get wrong and hard to rectify after the event.

[Little Aussie Battler]

I've done this, although it was to a different low-tax jurisdiction and not the CI.

In our case we kept the house and rented it out.  It was a massive hassle, and we only did it because it was in Sydney and we didn't want the transaction costs of selling and (potentially) buying back in later. Returns were terrible. Based on your comments so far I would definitely sell the house before you go.

We kept our Australian bank accounts open and visited occasionally, and still were deemed to be non-residents for tax. Anything you earn in Australia (dividends, interest, etc) will be taxed at the non-resident rate, which is quite punitive.  I would also run the numbers on selling your VTS and moving all investments offshore.

Finally, my experience of life on a small(ish) island was mixed. You've focused a lot on the positives (which I agree with), but you also need to consider the negatives beyond COL - particularly cabin fever and boredom for the trailing spouse, which we solved by (a) travelling a lot more than we ever did from Australia (at significant cost) and (b) having a baby.

Good luck!

[FIREupDOOON]

I've done this, although it was to a different low-tax jurisdiction and not the CI.

In our case we kept the house and rented it out.  It was a massive hassle, and we only did it because it was in Sydney and we didn't want the transaction costs of selling and (potentially) buying back in later. Returns were terrible. Based on your comments so far I would definitely sell the house before you go.

We kept our Australian bank accounts open and visited occasionally, and still were deemed to be non-residents for tax. Anything you earn in Australia (dividends, interest, etc) will be taxed at the non-resident rate, which is quite punitive.  I would also run the numbers on selling your VTS and moving all investments offshore.

Finally, my experience of life on a small(ish) island was mixed. You've focused a lot on the positives (which I agree with), but you also need to consider the negatives beyond COL - particularly cabin fever and boredom for the trailing spouse, which we solved by (a) travelling a lot more than we ever did from Australia (at significant cost) and (b) having a baby.

Good luck!

Thanks for the comment Little Aussie Battler

We were initially considering selling up. I’m aware I’ll be paying the highest marginal rate on rent - but still I’m a sucka who thinks the capital gain will be more over time (especially by leveraging debt in the property). Like you, my main fear is havin to buy back in and the cost of doing so (wherever we are).

I’m curious regarding your points on the negatives of Island life. Did your wife have a job? I imagine that’s a big factor in leading to boredom/cabin fever? Or was it that your work hours were significantly more than hers?

Ultimate question - would you do it all again?

[Little Aussie Battler]

If your rent isn't covering the interest expense, you probably won't have enough other income to get the tax benefits usually associated with negatively geared investment properties.  If you are planning to sell anyway when you get back, you are taking a big gamble on capital appreciation.

My wife didn't work. My hours varied, but even when I wasn't busy there wasn't much to do and only a very limited number of people to do it with. Finding fresh food that didn't spoil quickly was an ongoing challenge, and the healthcare system was hit and miss. There were also some cultural differences which seemed quaint at first but eventually became annoying. 

I'm not suggesting that it was all bad, just that any place you choose to live will have pros and cons.  Island life is no different.

I don't regret it at all, but I wouldn't do it again.

[redwagon]

I have not lived in Cayman but know others that have and I have lived abroad in a similar situation.
Would your employer be providing a housing allowance? This makes a big difference and you should negotiate for one if you can.
I'd also recommend budgeting for trips off island. Island life is awesome but you will probably want to get away from time to time.
Also keep in mind that many expats (and some locals), especially those earning big $$ will definitely NOT be mustachian which can be kind of annoying. I remember endless invitations to activities that were always $$$$. In Brisbane, I'm sure you can ignore these people and not worry about it but on an island (s) definitely not the same and may be more work to have much of a social life if trying to keep costs minimized .
And definitely consult an Australian tax accountant familiar with working abroad to ensure you get everything right  so you are not on the hook for anything unexpected.

[FIREupDOOON]

I have not lived in Cayman but know others that have and I have lived abroad in a similar situation.
Would your employer be providing a housing allowance? This makes a big difference and you should negotiate for one if you can.
I'd also recommend budgeting for trips off island. Island life is awesome but you will probably want to get away from time to time.
Also keep in mind that many expats (and some locals), especially those earning big $$ will definitely NOT be mustachian which can be kind of annoying. I remember endless invitations to activities that were always $$$$. In Brisbane, I'm sure you can ignore these people and not worry about it but on an island (s) definitely not the same and may be more work to have much of a social life if trying to keep costs minimized .
And definitely consult an Australian tax accountant familiar with working abroad to ensure you get everything right  so you are not on the hook for anything unexpected.

Hi Redwagon - thanks for the post!

Employer will not be providing a permanent housing allowance. Will be on my own for that!

Excellent point regarding other non-moustachians. Here in Brisbane I have a circle of family and friends who at the very least try to understand my way of life. I imagine I’ll meet plenty of people over there who earn $250US (tax free) and have nothing to show for it at the end of the year.

Not too sure how to manage that - but I’m sure I’ll find a way.

[Lukim]

I have never visited the Cayman Islands but I have friends who worked in the "offshore" industry in the British Virgin Islands (which I hear is geographically much nicer than the Caymans).

I have also been a long term expat (but never on a small island) - now live in an extremely large busy Asian city.

I think as long as you regard it as a 3-4 year exercise it is doable.  My friends who were in BVI lasted 2-3 years and only managed to last that long as they were regularly flying out every weekend etc.

I am also very familiar with the Brisbane property market - do not expect much in terms of capital gains in the next 4 years. At best, the Brisbane market will be flat (while Sydney and Melbourne markets fall).  If you were somewhere in the inner city in Brisbane you may be ok.

Keeping your former place of residence (house) can work against you in terms of Australian tax residence but it sounds like you are cutting most of your other connections so you should be ok as being a non resident.

When you go back to Australia as a resident, you need to be careful about keeping investments in tax havens - you may be better off bringing the investments into Australia as cash or moving them to less "red flag" jurisdictions such as Singapore or Hong Kong.

As someone who has been an expat for more than 30 years, I would say go for it.  Don't expect it to make you FI in 4 years, that is a long haul.  I have been FI for quite a number of years but being an expat gets in your blood and I find I keep working (I need to have a work permit in order to keep residency, not because I need the money).

Good luck

[SimplyMarvie]

I have lived and worked in Cayman, and I don't think this is a particularly great plan.

I think you're under-selling the huge costs of living in Cayman, which other people have already pointed out. More concerning, I don't think you're thinking particularly clearly about what the Caymans are like to live in -- they're small islands that are mostly scrub-brush with not a lot going on for people who live there. There's a very strong divide between native Caymanis and outsiders who come in for work, and then again between people on permits and those who actually have Caymani citizenship, which ends up limiting your social circle significantly. The Caymanis that I knew actually worked pretty hard and long hours. Your commute is short and you can go sit on the beach when you're done with work, but it's not this tropical easy-breezy 30 hour a week BS that I think a lot of people assume (and honestly, if you know a place like that let me know... maybe then I can convince Mr. Marvie to give the Tropical Island thing another try!)

Island fever is absolutely a thing -- there isn't much to do on Grand Cayman (and even less on the sister islands) and most of it is geared toward tourists and cruise ship passengers, so you run out of things to do on the weekend quickly. The Caribbean in general is not well connected either by ferry (Cuba puts a geographic wrench in the works) or by air, due to trade protectionism related to national airlines, which meant the only place we could go cheaply by air was Kingston, Jamaica. Everything else pretty much involved transiting through Miami and high airfare. Feeling utterly stuck, with no where to go on the island and no real way to get out sucked balls.

If your wife isn't working, what else is she planning on doing? I've done the expat thing where you go to work and immediately get a cellphone and a peer group and something to do while your spouse is left sitting at home wondering what they've done with their lives -- it's a recipe for misery, depression and divorce, and divorce is expensive.

[chasesfish]

I'm glad to see someone who's lived and worked on the Cayman's post.  We've visited and rented an apartment to get a more local sense of the place than the resort experience.  We are generally laid back people and were bored in a week. I've visited and want to echo what @SimplyMarvie said:

- Its a small island full of scrub brush.  When I say small, its really small.  61,000 people total, probably 2/3rd residents, 1/3rd expats.  The residents work in tourism, expats in banking/insurance. 

- You basically have the beach plus snorkeling, limited surfing, very limited depth so unknown on fishing.  We visit the carribean and Hawaii and like to do other activities and just didn't find them here.

- We didn't find cost of living that insane if we stuck to buying our food at CostULess, their knock off of a Costco.  If it has to be refrigerated and shipped, expect to pay.  No different than other islands.

- Your best entertainment will be befriending other expats and sitting on the porch or on the beach with a cold one in hand and enjoying the company of others.  We observed limited shopping/nightlife/affordable dining.   Plenty of mediocre restaurants will happily take $200 from you, but that defeats the purpose of working somewhere for more money.

- If you like the occasional big city experience, expect to spend the $1000 to $2,000 to go fly and spend a weekend in one of the nearby US cities with direct flights (Miami, Dallas).  One observation was some of the expats could make so much money there it still made sense to "fly off the rock" one a month and get their fix for someplace else.