Retirement plan to support my "habit"

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gee, do you think it might have something to do with the active volcano on the island?
I shouldn't have laughed out loud reading that. But I did. So thank you.

...it highlights a good point too... Paradise isn't always what people imagine it to be. I have friends who retired to sail the world... Made all the years of sacrifices. Preparations... Etc... Two weeks in, realized they hated it. Sold the boat at huge losses and tried to rebuild a new dream.
 
Yeah, normally we're snowbirds 3 months (Jan.-March) on the FL panhandle, which may cost us about $5K in condo rentals--not bad for 3 months. It's the off season on what they call the "Tundra", and shore diving is just OK, boats go out weather and no. of divers permitting. S. FL condo rental costs are considerably more, off season (summer for there) or not.
I am curious about the "complicated" Ontario healthcare rules, as I was under the impression that all provincial systems are the same in requiring 180 days residing in Canada. I'm surprised to hear that is incorrect. Can you provide me some basics about the Ont. system? Just curious.

I have to admit, I did not read these carefully, but just scanned them for quick info:

Snowbirds, Don't Risk Losing Your Provincial Health Care Insurance!

According to this website, you are correct that in NS, the rule is:
  • Must be physically present in Nova Scotia for at least 183 days in any 12 month period.
Note that I did not do additional research for NS except for the link above. You can see that the rules are different by province.

For Ontario, it appears the magic number is 153 days but with additional criteria. See link below:

https://www.ontario.ca/page/apply-ohip-and-get-health-card#section-2
See, in particular, “Who qualifies” and “Reapplying for OHIP”.

And add to that this exception:

https://www.ontario.ca/page/ohip-coverage-while-outside-canada
See, in particular, “Away for more than seven months”.
 
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Maybe someday Turks & Caicos will become the 11th province--there has been talk of that, but I'm not holding my breath. And that place may not be so cheap to live anyway.

We can only hope. I think we got screwed at some point. It seems like every other country has Caribbean island except Canada. We get to chose between cold and colder.
 
. . .
As a Canadian, I’m going to have to maintain ties to Canada to maintain my healthcare. So I cannot be away for the whole year.

There's the rub for those of us in the US. If we retire in the US, health insurance and healthcare will likely be our greatest costs in retirement. Sure, Medicare kicks in at age 65, but I wouldn't count on it, and I'm not going to wait until age 65 to start diving more and working less. Right now, besides the loan payment on my home, health insurance/healthcare is my biggest expense by far, and it seems unlikely this will be different in retirement. This why retiring outside the US, in a country with good healthcare, or even a program the benefits expat retirees, is looking attractive.
 
Referring to that other thread about buying property in Cozumel, my thinking has switched instead to Grand Cayman for several reasons: British commonwealth island, familiar laws, job opportunities in finance/legal/banking, no income/capital gains tax, fairly easy to import pets, etc. This is despite Cozumel being less expensive in day-to-day living. It’s a thought.

If you want more info about it, I am happy to share our experience (especially regarding importing pets!)
 
If you want more info about it, I am happy to share our experience (especially regarding importing pets!)

Thanks for the offer! First task...see if my skills will find me a decent job on the island. :D
 
Very interesting topic to me so I'll throw my .02 in.

Mrs flush and myself are 44 and 48 respectively. This is the second marriage for both she and I. We were both terribly stupid with money earlier in life with our first spouses. Some because of them, some because of us. If we had been practicing then what we practice now then we would probably both be very close to retiring, if not already. Even at that we think we can be looking seriously at retirement in 10 years if we remain in country.

We will have the kids out of high school at that point. We do not live like paupers but neither of us throw money around willey nilley either. We have one note a month and that is our house which we hope to have paid off in the next 4 years by making double payments. Everything else is paid for including cars and we pay cash for everything else (not exactly cash but if we do not have the money to buy it outright then we do not buy it)

In general terms we save/invest half of our income per month. Expenses and (current fun money) are the other half.

We think our plan is to sell the house and move somewhere with good diving. Some will depend on where the kids decide to go to college if they go that route. They are half Aussie so I am pushing that direction :wink:
 
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I think that it might be a little easier for Canadians to immigrate and find work on British Islands like the Caymans and T&Cs because they are all part of the British Commonwealth, I've met a lot of Canadians living and working there - but that's just a guess.

I've also met many folks working in the Caymans that are unhappy about the "work permit term limit" for foreign workers, see below. They can't get work permtis for longer than 7 years and they can't apply for permanent residency until they have lived there for eight years.

So they find a job, get established and then have to leave for 2 years and start over. During our last trip we were speaking with a bar tender from the US who said that she had previously worked as a Dive Master for Red Sail on Grand Cayman, but had to leave when her work permit expired. She was eager to return to Cayman and managed to find a bartending job when she was eligible to return.

If I were to retire to someplace warm with tropical diving it would probably be in the US, like Florida (or Hawaii - if only I could afford it!) or one of the US Caribbean Islands, so I wouldn't have to worry about immigration and healthcare and work permits.

I remember sitting at the bar at the Cayman Brac Beach Resort a few years ago and talking with the dive shop manager, I can't remember his name at the moment, but he told me that he would soon have to leave because his work permit would expire and he wasn't sure what he would be doing. I'm pretty sure that he was from the US. A few year later we encountered him again and he was back in Cayman as the general manager for the Little Cayman Beach Resort. I recall hearing that he and the dive shop manager (Sharon) had gotten married. Sharon said that she was from South Africa and I think that she is now a Caymanian Citizen. So it sounds like they have found their place and will likely remain in Cayman for a long time - I am glad because they are good, hard-working people and deserve to be happy.

One day when we were out and about on the island of Cayman Brac a couple of years ago we bumped into Barb, the popular divemaster at Cayman Brac Beach Resort, and she introduced us to her daughter and husband. He was was born in Cayman and works in the local fishing industry. Barb said she was originally from Canada but has been happily settled in the Caymans for years, so they are another example of nice people that have found the best place for them.

So living and diving on a tropical island is not an impossible dream, but I don't think that it is very easy to arrange.

Term limit
Seven years is the maximum length of time a work permit holder can work continuously in the Cayman Islands. After this period the board cannot normally grant the person any further work permits until he or she has left the Islands for at least two years. The only exceptions to this would be a worker designated as an 'exempted employee' in a business staffing plan, or where the board considers that there are exceptional circumstances. In such cases the board may, at its discretion, grant additional work permits to enable the person to complete an aggregate period of eight years, thus making him eligible to apply for the grant of permanent residence.
 
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I think that it might be a little easier for Canadians to immigrate and find work on British Islands like the Caymans and T&Cs because they are all part of the British Commonwealth, I've met a lot of Canadians living and working there - but that's just a guess.

I've also met many folks working in the Caymans that are unhappy about the "work permit term limit" for foreign workers, see below. They can't get work permtis for longer than 7 years and they can't apply for permanent residency until they have lived there for eight years.

So they find a job, get established and then have to leave for 2 years and start over. During our last trip we were speaking with a bar tender from the US who said that she had previously worked as a Dive Master for Red Sail on Grand Cayman, but had to leave when her work permit expired. She was eager to return to Cayman and managed to find a bartending job when she was eligible to return.

If I were to retire to someplace warm with tropical diving it would probably be in the US, like Florida (or Hawaii - if only I could afford it!) or one of the US Caribbean Islands, so I wouldn't have to worry about immigration and healthcare and work permits.

I remember sitting at the bar at the Cayman Brac Beach Resort a few years ago and talking with the dive shop manager, I can't remember his name at the moment, but he told me that he would soon have to leave because his work permit would expire. A few year later he was back in Cayman as the general manager for the Little Cayman Beach Resort and I seem to recall hearing that he and the dive shop manager (Sharon) had gotten married. I remember that Sharon was from South Africa and I think that she mentioned that she was now a Caymanian Citizen. So it sounds like they have found their place and will likely remain in Cayman for a long time - I am glad because they are good, hard-working people and deserve to be happy.

One day when we were out and about on the island of Cayman Brac a couple of years ago we bumped into Barb, the popular divemaster at Cayman Brac Beach Resort, and she introduced us to her daughter and husband. He was was born in Cayman and works in the local fishing industry. Barb said she was originally from Canada but has been happily settled in the Caymans for years, so they are more nice people that have found the best place for them.

So living and diving on a tropical island is not an impossible dream, but I don't think that it is very easy to arrange.

Term limit
Seven years is the maximum length of time a work permit holder can work continuously in the Cayman Islands. After this period the board cannot normally grant the person any further work permits until he or she has left the Islands for at least two years. The only exceptions to this would be a worker designated as an 'exempted employee' in a business staffing plan, or where the board considers that there are exceptional circumstances. In such cases the board may, at its discretion, grant additional work permits to enable the person to complete an aggregate period of eight years, thus making him eligible to apply for the grant of permanent residence.

@KathyV , interesting. I didn’t know that the magic number was 7 years. That is, of course, ok with me as my intention is not to be a Caymanian full-time. I’d lose my Canadian healthcare coverage by doing that. I would like to be what we Canadians call a “snowbird”, fly south in the winter, fly back home in the summer, so we can keep our healthcare. Free healthcare is a big deal, especially in old age!
 
. . . Even at that we think we can be looking seriously at retirement in 10 years if we remain in country.

. . . We have one note a month and that is our house which we hope to have paid off in the next 4 years by making double payments. . . .

We think our plan is to sell the house and move somewhere with good diving.

If you plan to retire and sell the house 10 years from now, does it make sense to pay it off in the next 4? My thinking has been that, so long as the tax laws continue to allow us to deduct mortgage interest, I am better off using that deduction against my income and stashing as much money away as possible in my retirement/investment account than using that money to pay off the loan early. I could pay the house off now using money I have saved for retirement, but that never seemed like a good plan to me.
 

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