“Kathleen, 
“Perhaps it’s time for me to re-read your book, but I would greatly appreciate any advice you could provide. I’m wondering, for example, about a rough range of what I should estimate for relocation expenses (we’re a family of four–two adults and two children who will be going to high school by the time we can seriously consider this move).”
–Dallas K., United States
Lief and my plan has been a work in progress for more than a dozen years and is still evolving. As you say, our intention long-term is to spend time in four places: Paris, Istria, Medellin (which we’ve substituted for Buenos Aires), and Panama. In Panama, we want a house at the beach but will also need a place in the city. As our business is based here, we’ll always be coming and going, no matter where else in the world we decide to spend time.
We decided long ago that we’d invest in owning residences of our own in each of the locales where we knew we wanted to spend time long term. For us it’s been part of an overall investment strategy. But buying and maintaining residences in four countries takes time. So, again, this is still a work in progress.
So far, we have the backbone of the plan in place with apartments in Paris, Panama City, and Medellin, all of which are rented when we’re not using them. We’ve bought a farmhouse in Istria, Croatia, but it’s still in need of renovation. And we have the land for our beach house in Panama (at Los Islotes), but we’ve yet to begin construction of a house there.
Of course, you could pursue this approach to “retirement” without owning in all four places. You could rent short-term as you move around, as friends have done. The difference is that you have children, which I think would make that approach more complicated. The fact that we also have two children is part of the reason we decided in the beginning to invest in homes of our own in the places where we knew we wanted to be. With children, you’re more concerned about having roots, about nesting.
Also, with children, schooling is a priority part of any plan. This is why we won’t be able to put our plan into effect in full until our son goes off to college. That’s seven years away. Meantime, our schedule is largely dictated by his school calendar.
There are many complications associated with the approach Lief and I have decided to take. One advantage, though, is that, spending less than three months at a time in each country, as we plan to do, we don’t have to worry about residency visas, which are a hassle and an expense.
One advantage of owning rather than renting as we move around is that the places where we aren’t can always be rented out. That’s roughly nine months of rental potential per property per year, give or take, which should amount to a nice cash flow long term.
Our biggest expense, given the approach we’re taking, could be travel. Getting from Croatia to Medellin, for example, is tricky and costly. You’ll want to take travel logistics into account when mapping out your strategy big-picture.
