Illuminating the challenging choices investors, foreign property owners, and pondstraddlers make when crossing borders.A pondstraddler is a person with multiple citizenships who has a foot in more than one country across the North Atlantic pond and whose heart is in both places. This group in particular have many issues to face.But why would anyone want to focus on life planning mishaps? Isn’t it hard enough just to get through the day, week, and month without some smart-aleck writer negatively pointing out, after the fact, a poor financial decision that was made?One big reason and several small reasons that we (I’m not alone) bring these facts to the forefront is because we are: a) human and b) we tend to make the same mistakes, more than once. The fact that the financial, legal, tax, and immigration data behind a decision-making process is constantly evolving does not help.1. We impulsively — even though we think aren’t (and are determined we won’t) — tend to follow the herd in the investing decision process. For example, if everyone is doing it, such as buying stocks at an accelerated pace because a capital market is skyrocketing, it must be right for us, too. Safety in numbers, right?2. We don’t take the time to consider the big picture impact on our personal financial profile. This lack of substantive research can be a very damaging decision when applied to purchasing property, residing, opening investment accounts, operating a deemed business (either as a shareholder, officer, or partner), or implementing an income generating plan in an another country3. We have lost faith and trust with financial salespersons to give us an unbiased, conflict-of-interest-free advisory opinion.Unabated, this distrust has increased in recent years due to the malfeasance and manipulation of financial data in the arenas of capital, mortgage and real estate markets by those who have not upheld their fiduciary duty to perform in the best interests of their clients. This lack of trust and confidence in financial advisers was articulately explored by a fellow columnist in this newspaper last week.Generally, when we make serious financial decisions whether in real estate, investments, personal property (collectibles, cars, etc) we tend to succumb, more often than we would like to admit, to our emotional side rather than focusing on the analytical full facts decision making process. And then, regrettably, we get to spend considerable time and money cleaning up the less-than-desired results of said decisions.Last week, the Moneywise column focused on the dream of many Bermuda residents to leave our sparkling pink and turquoise shores to move to the United States for full or part-time residence.A number of readers responded, either in the commentary section or in e-mails to me, personally.As expected for such a significant move, misunderstanding and misperceptions of US immigration, financial, and regulatory requirements was prevalent.Predictably, the US citizenship-based taxation structure was never mentioned, indicating to me, again, that Bermuda residents, most never having been exposed to an income tax regime, cannot fully grasp the enduring complex challenges of US tax (IRS) compliance and its correlation with US Customs & Immigration Services (USCIS).There is an assumed presumption that entry into the US is as easy as an individual walking across the border, buying property, and then setting up a household.In broad general terms, unless you have a legitimate current US passport, your entry approval into the country may be based on a number of factors, both yours and the USCIS border crossing officer’s knowledge of your personal situation and later the IRS.These are some of them:— Your nationalities, and citizenships— Details of your family’s nationality and citizenship going back several generations, in some cases— Your residency category, and your connections to other countries— Your upstanding citizen quotient and reputation— Your “deemed” US status viewed from the US perspective— The number of days you have spent in the US for the current year, and at least, the three prior years (although further back) may be required documentation— Your perception and understanding of your tax compliance responsibilities under a citizenship based taxation system (US) versus a consumption-based regime (Bermuda), and tax treaty country regimes— Your plans for working, investing, operating a business, retiring, education, etc— Your ties (former and current) to the USWhen a specific entry permission from US immigration authorities is granted, in the form of a visa/letter for a spouse of a US citizen, a foreign student, foreign employee, etc, and with your acceptance of that permission, you are acquiescing to obey and observe all American laws, including those that apply to the US taxation regime applicable to your personal situation.I thank readers for their responses and commentary.Given space constraints, I was not able to comment on all questions and statements received, or provide a summary of the citizenship purchase programme and foreign pension withdrawal as promised.Instead, we will make the ‘pondstraddlers’ dilemma’ a regular monthly feature on the last Saturday of each month.Please send in your questions and commentary to my e-mail address. They will be answered without revealing any personal information.The information contained within this article cannot be, nor should ever be, used as a substitute for detailed qualified individual United States tax, immigration, legal or financial, regulatory advice. I emphasise and reiterate the statement made in last week’s article, “the United States worldwide citizenship based taxation structure could dematerialise your entire personal net worth acquired prior to your relocation. No one should plan for such a serious inbound lifestyle change without serious work in structuring all offshore assets appropriately.” I highly recommend that if you, dear reader and your family, are entertaining such a move that you consult with an experienced cross border financial planner specialist, first, first, first. Always plan before you purchase!Martha Harris Myron JP CPA PFS CFP TEP is a Bermudian, and a cross border financial planning journalist. Her articles are published domestically and internationally, focusing on the challenging financial environment for local and international residents and their families living and working in Bermuda with connections across the pond in the North Atlantic Quadrangle: United States, Canada, United Kingdom and Europe. Inquiries to martha.myron@gmail.com