After spending a career as a weapons engineer, one of Jeff Runyan's clients was ready to live out his retirement adventure. He and his wife bought a sailboat and planned to spend their time as expats sailing the seven seas.

A year and a half in, however, Runyan, a Los Angeles-based independent advisor with Wedbush, got some unexpected news on Skype—they were cutting the journey short. It was not a medical emergency or sudden family crisis that sent them back home. It was boredom. After days spent fixing equipment, waiting out bad weather or waiting to find fresh food, the engineer and his wife realized that their dream of retiring on the high seas was turning out to be pretty dull.

As more clients look to live out their retirement dreams abroad, whether on a boat or on a foreign coast, advisors need to be ready to deal with the unexpected issues that can crop up. Around 350,000 Americans are already receiving their Social Security checks abroad and an estimated 3.3 million baby boomers are considering living outside the United States, David Vequist, founder and director of the Center for Medical Tourism Research in San Antonio, Texas, estimates.

"I can see people wanting to give it a try, especially with life expectancy increasing the opportunity to do something different," Runyan says. "Sixty is the new 30."

Ameriprise advisor Harish Vishria calls them his 21st century snowbirds. Some seek cultural fulfillment, others are drawn by the lower cost of living. Whatever the case, would-be expats will face a number of difficult decisions. Although as many as 15% of the Memphis, Tenn.-based advisor's clients talk about going abroad, only half of that end up making the move.

"For wealthy people with property and business interests, it's more difficult," says Dean Deutz, a senior manager at RBC Wealth Management who works on a team advising high net worth clients with assets over $5 million. "They go through an analysis and realize they could maybe move to a different country and save some tax money, but now they have all this complexity and see their family less."

When a client brings up the topic of moving abroad, Runyan starts with a few top-of-mind questions such as how they chose their location, what they plan to do while they are there and if they are planning to work. Then, they can move into some of the thornier issues.

Housing Predicament
When helping clients who want to retire abroad, the first problem is deciding what to do about their U.S. residency. Maintaining a home or business may mean that clients will have to continue to pay state income tax or property taxes, association fees and insurance, which can quickly outweigh the lower cost of living abroad.

But giving up residency and leaving the state tax system is no easy task, according to Deutz, who is based in Minneapolis. States that have a state income tax, like Minnesota, New York and California, "don't let their residents go easily," Deutz says.

In Minnesota, for example, you can give up your house, but you are not allowed to spend more than 183 days in the state unless you are paying income tax. Often, the state will audit those who change their residency by checking airline tickets, credit card records, hunting licenses and other documentation. Many clients also have business interests in their home state, which adds to complications and often requires bringing on a tax attorney, Deutz says.

With that in mind, many clients opt to keep their house and residency. They hold the majority of their assets in the United States and wire funds to their new home country as needed in order to avoid paying double taxes, Vishria says. Because almost all clients keep their U.S. citizenship, they still pay income tax, even on earnings in their new home country (although they get a tax credit for foreign taxes they pay). Runyan also helps clients find creative ways to make up for having two residences, such as renting out the home to a family member, which can double the savings.

Once that is settled, there is the question of finding a home in the new host country. In Mexico, for example, the government wants to retain control over valuable ocean-front property, so there are prohibitions on U.S. citizens and foreigners buying property on the coastline, Vishria says. His clients often have to purchase the home through a trust, although the trust, and thus their ownership, is only valid for 99 years.

Health Care
Health care can be a major motivation to move, especially for clients looking to save money. Clients can take advantage of cheaper health care in other countries and continue to benefit from supplemental Medicare coverage. Vishria recommends Medicare Plan F or G, both of which offer some international support.

Minor medical care is very good in other countries, Vishria says. Standard medicines and prescriptions are also usually available, but Vishria does not recommend relying on foreign insurance or hospitals for major emergencies. For example, insurance policies in other countries often send patients to the hospital closest to where they live for treatment even though that may not be the best care facility. Vishria requires that all clients moving abroad purchase extra insurance that will transport them stateside in case of a medical emergency.

In fact, medical concerns bring clients back home most often. As they age, need more intensive health care services and look to be closer to their family, keeping the U.S. residence looks like a very wise decision, Vishria says.

Lifestyle Concerns
The conversation about retiring abroad goes beyond financial and logistical concerns. As their primary advisor, you should be prepared to take a big picture look at what the move would mean for clients' personal lives and prepare them for seeing their family less, as well as other emotional stresses.

"When you're living out that goal of retirement the way you've envisioned it, you realize all these unexpected events like boredom and downtime," Runyan says. Since he is about half the age of most of his potential expat clients, Runyan tries to be sensitive when addressing some of these concerns. "I have to deliver it in a way that I don't sound patronizing," he says. "But there are genuine concerns that you know exist for others who have already been down that path."

Issues can vary depending on location, but his clients have run up against everything from daytime mosquitoes to having to wash fruits and vegetables in 10% bleach solutions. "It's not just a tropical paradise at the Four Seasons," Runyan says.

Keeping in Touch
Moving also presents some logistical challenges for advisors. Rules about working with U.S. citizens who have moved abroad vary by firm. Ameriprise does not permit advisors to work with clients in other countries, so Vishria has to set up a proxy for those clients. Most of the time, they assign power of attorney to a son or daughter still living in the United States so that Vishria can continue managing the money.

"I still continue to make investments based on their time period and what they might need based on their new lifestyle," Vishria says. "That doesn't change, but the method in which we communicate with them changes."

Vishria has five different time zone settings on his clock, so he can schedule meetings with clients as spread out as London and Mumbai. He takes into account different holiday schedules as well. For example, the weekend for his Middle Eastern clients is Thursday and Friday. He relies on technology and secure websites to update account information and spends a lot of time in front of the camera as he looks to keep conversations personal across long distances. "Skype is my best friend," Vishria says, laughing.

Both Runyan and Vishria suggest a trial period as a good way for clients to get a taste for the local atmosphere of their potential retirement destination. After working through all the angles of their decision, Runyan advises clients to spend three months in the foreign country and then decide if they want to stay. That gives clients time to either fall in love with their new home or get bored, Runyan says.

Deutz has what he calls the "global retiree" alternative. Global retirees retain their residency and U.S. citizenship, but satisfy their wanderlust through frequent travel rather than a permanent move.

"That's what we see most often," Deutz says. His clients say, "'I have enough money to live where I want. I'm going to do what I want rather than being driven by saving some dollars on taxes.'"