An Expat Financing & Cash Flow Adventure on Grand Cayman: the Pursuit of a Rooftop Terrace

by Anne Evans

Just in case you thought otherwise, our transition from our former “forever” residence as US Citizens in St. George, UT to Resident Expats in The Cayman Islands (TCI) was not done on a whim. It was carefully researched and planned. However, best plans can go astray — as the saga of our Rooftop Terrace explains.

How We Purchased our Condo

We committed to purchase our “penthouse” condo on Grand Cayman in The Cayman Islands before it was built and without ever having been on Grand Cayman!

We had no choice. COVID prevented traveling to TCI, and properties there were selling fast. With the help of our financial advisor, we worked out a plan to either liquidate or take out a short-term loan on various aspects of our nest egg, so we could purchase the condo with cash. Then, after closing, we planned to take out a nominal home equity line of credit (HELOC) to pay back the loans and finance some of the additions to the condo and other expenses we anticipated. We opened “Premium” status accounts with a well-established international bank on Grand Cayman well in advance of departing the US, and we were told by the bank VP who assisted us that it would not be an issue to obtain a HELOC after we closed on our property.

The Roof Top Terrace – before

When we finally arrived on the Island, we found that our new home was just what we expected: quality construction and finishes, modern and with spectacular views that were and still are probably the best in the development. The “cherry on top” was our private Rooftop Terrace – 1236 sq ft of empty space but with interrupted 360-degree views. The views extend to the east of the canal our condo was built along and beyond to the North Sound, to the south for a view of Camana Bay, and to the northwest encompassing the West End of the island which parallels 7-Mile Beach.

It was just begging for an outdoor kitchen complete with a built-in grill, pizza oven, large dining table with chairs and an array of comfy patio furniture.


We closed on the condo the day after we arrived on the Island and began to move in. Paperwork was completed on the loan, submitted and we waited . . . and waited. The bank VP who helped us establish our accounts had moved on. No one at the bank was helpful. Our short-term loans were coming due. Finally, the bank gave us an answer: “No.” Despite owning our condo free and clear. Despite having stellar credit ratings. Despite our other non-real estate assets. Despite having documented significant annual income. The answer was “No” – with no explanation. Applications to other banks on the Island garnered the same “No” – also without any helpful explanation. After some conversations with new local friends that were in the Island’s financial industry, we learned that HELOCs simply are not a product offered in these Islands.

So, we decided to apply for a mortgage instead and received a chorus of “No’s” from each bank we applied to. The explanation was simple. Mortgages are not made available to retirees on the Cayman Island – no matter their documented wealth.

We still maintained our “Private Client” status accounts with our US bank so perhaps they would give us a mortgage? “No” – because our property was on foreign soil.

Cash Flow

To add to our challenges, the US government was withholding our Social Security (SS) cheques. Rick’s was being withheld because the Social Security Administration (SSA) could not understand how to wire the funds to our Cayman Island Bank. I initiated my SS payouts after we arrived on the Island, however no checks were received. After 3 months, I started calling the Social Security Administration. (FYI – should you ever need to call the SSA, set aside an entire day to wait on hold trying to get through; not kidding.) No one could tell me what the problem was. To cut a long story short, the SSA seemed to think that I might be receiving a pension from TCI. I explained that this was impossible, because I had only been on the Islands for 6 months and the nature of my Residency did not permit me to work. Nine months in, I finally started to receive my SS checks, including past due monies. At least that first one was a whopper!

Cash flow became really tight those first 6 months on Grand Cayman. I tried to buy us time to get our income straightened out by applying for credit cards offering a no interest introductory period.  (This was instead of using our current credit cards that weren’t offering a no-interest period.)

My initial attempts were by telephone, and I immediately learned that since we no longer had a US physical residence, our applications would be rejected. And even though I applied to those same banks where we had never missed a payment on prior credit card accounts, no one would approve us. I finally got around this issue by applying online and using the Florida address of our Postal Store . . . without our PO Box number. (Interestingly enough, there are no Cayman-based banks offering credit cards.)

The good news is that after 14 months into our transition to Grand Cayman, our cash flow was stabilizing in line with our original expectations, and our short-term debts and most of our expenses associated with our move were cleared. We were no longer “treading water,” and we were beginning to tackle our list of additions to the condo and other expenses we had originally anticipated covering with a HELOC. This was now an exercise in prioritization:

  • We leased a car (maybe next year we will be able to afford a car)
  • We completed or at least initiated most of the indoor condo improvements (e.g., expansion of cabinetry, appliance upgrades, critical furniture additions)

All of these expenses took priority over building out the Rooftop Terrace as well as adding solar power.

We had a walk-in area for long term storage on the Rooftop Terrace so I was up there most days to access that enclosed area. Often, I would take a moment to pause, be amazed by the views and the generous living space that was ours, knowing that someday it would indeed be lived-in space.

The Rooftop Terrace – under development

It was Fall of 2023 when we took our first steps toward realization of our Rooftop Terrace dream – to be completed on “Cayman Islands Time”:

  • July 5, 2023 – Initiated design and construction of Rooftop Terrace outdoor kitchen.
  • Sept 2, 2023 – Pizza oven purchase from Home Depot in the US for importation. Delivered to our condo Sept 26, 2023
  • Nov 28, 2023 – Gas grill purchased from A.L. Thompson on Grand Cayman Island
  • Dec 22, 2023 – Completion of Rooftop Terrace outdoor kitchen (excepting some electrical wiring hiccups pertaining to the pizza oven)
  • December 23, 2023 – first use of built in gas grill.
  • Feb 6, 2024 – first use of pizza oven

The Rooftop Terrace – what’s next


All in due time.

After all, “good things are worth waiting for”.

If ai cannot solve a problem by baking a cookie, I cannot deal with it

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