Retirement plan to support my "habit"

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@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!

"Snowbird" is a species we also have in the US! Healthcare is a big deal, especially as you get older, but I don't think that your healthcare in the tropics will be covered by your Canadian policy - at least that's how it is for Medicare in the US.

My advice is not to wait, but find a good financial advisor now and do what he/she says!

You might also look into buying property that you can use both for on-island living and rental income when you are not using it - but you would need a property manager. I think that is what @EastEndDiver does with his condo at Turtle Nest Inn on Grand Cayman.

It occurs to me that he was smart for doing this because we have spent a lot of money visiting tropical islands on vacation over the years when we could have been building an investment; but I also worry because the tropics are subject to hurricanes, typhoons, and other disasters! I wonder if you can get good storm insurance in the tropics and if so, it is horribly expensive?
 
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"Snowbird" is a species we also have in the US! Healthcare is a big deal, especially as you get older, but I don't think that your healthcare in the tropics will be covered by your Canadian policy - at least that's how it is for Medicare in the US.

My advice is not to wait, but find a good financial advisor and do what he/she says!

Haha, yes, FL is inundated with snowbirds at certain times of the year!

No, our Canadian healthcare doesn’t cover us when we leave the country. The plan is this: I find a decent job in the Caymans before retirement that will include adequate healthcare coverage. My skills will be in the finance/legal/banking area so I expect there will be healthcare benefits. I buy a home and pay it off slowly. I need to leave in 7 years (unless I fall into an exemption), so I’ll rent that home out. I’ll visit every year. When I’m ready to retire, I’ll live partly in Cayman and partly in Canada. When I live in Cayman I’ll have to buy my own health insurance. Sounds nice, but just a dream now. I have to do some job searching first to see if it even makes sense!
 
look @Dog Bowl whos to say you cant work while retiring ? im in that phase I am a retired full time diving instructor I have had several offers to retire in the islands even had a friend offer his dive shop for free to me (as long as I kick back a percentage ) so its not all doom and gloom ...we will talk at the deep 6 clinic ..bet I can give you some great ideas how you can have your cake and eat it too with diving and retiring
 
look @Dog Bowl whos to say you cant work while retiring ? im in that phase I am a retired full time diving instructor I have had several offers to retire in the islands even had a friend offer his dive shop for free to me (as long as I kick back a percentage ) so its not all doom and gloom ...we will talk at the deep 6 clinic ..bet I can give you some great ideas how you can have your cake and eat it too with diving and retiring

Haha, sure... but don’t mention in front of my husband the part about moving to a foreign country. He has no idea about this secret plan of mine! Lol
 
Thanks for the offer! First task...see if my skills will find me a decent job on the island. :D

You might want to check into the regulations about working in Mexico. Getting a "job" might be challenging (unless you have skills that the locals don't have) but it seems to be OK to have your own business.
 
Haha, yes, FL is inundated with snowbirds at certain times of the year!

No, our Canadian healthcare doesn’t cover us when we leave the country. The plan is this: I find a decent job in the Caymans before retirement that will include adequate healthcare coverage. My skills will be in the finance/legal/banking area so I expect there will be healthcare benefits. I buy a home and pay it off slowly. I need to leave in 7 years (unless I fall into an exemption), so I’ll rent that home out. I’ll visit every year. When I’m ready to retire, I’ll live partly in Cayman and partly in Canada. When I live in Cayman I’ll have to buy my own health insurance. Sounds nice, but just a dream now. I have to do some job searching first to see if it even makes sense!

Sounds like a good plan because (as I am sure that you already know) Cayman has a huge financial and banking industry!
 
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.

That is a good point and one that we looked at in pretty good detail @Lorenzoid . We decided that we wanted to work toward paying it off for two reasons.

1) what we are getting to deduct in mortgage interest is becoming pretty small due to what we have vested in principle of the original loan and we feel like we are going to be better having that money working in some higher growth options.

2) Like I alluded to in my earlier post, we both worked ourselves into a terrible financial hole earlier in our lives and we both pulled ourselves out of it by our bootstraps vowing never to be in that position again. Paying off the house is personal to both of us in that regard. When we decided a few years back to first get serious with each other in lieu of doctors tests we examined each other's credit report.
 
You might want to check into the regulations about working in Mexico. Getting a "job" might be challenging (unless you have skills that the locals don't have) but it seems to be OK to have your own business.

I’ve considered Mexico. Cozumel, of course. Unfortunately, I would not be very employable there. Grand Cayman, on the other hand, is much more up my alley. I might have to go backwards a few steps, but it’ll still be within my realm of possibilities job-wise.
 
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