Leona Helmsley was already famous when she uttered the now immortal words: “Only the little people pay taxes.” Still, this ushered the Queen of Mean into the ranks of tax history in ways neither she nor the maid who reported the quip could have contemplated. Mrs. Mean would later achieve additional notoriety in the estate planning department with her $12 million bequest to her beloved dog, a Maltese named Trouble. See Helmsley’s Dog Gets $12 Million in Will.

The hotel baroness’ forays into tax planning were most famously of the sales tax and business versus personal variety. Nevertheless, her little people quote surely sums up what many people feel about the rich: their rules are different. The IRS may have taken a page from Mrs. Helmsley’s book in setting up its new Global High Wealth Industry Group. See ‘Audits From Hell’ Target Rich. Some now call this “The Wealth Squad,” but I like to call it “The Rich Squad.”

The Rich Squad is just getting started, but if you’re rich (more about what that might mean below), start getting your ducks in a row. Otherwise you too could end up with a Maltese named Trouble. Keep good documents and records, since if you ever have to go down this road much of the audit process will be providing copious copies of just about everything.

How Rich is Rich? This may be the question of the ages, right up there with the meaning of life, but no one seems to be saying just how rich you have to be to get targeted by The Rich Squad. Still, there are some figures available. The Rich Squad is part of the IRS’s Large Business and International Division.

That generally means more than $10 million in assets. Assets and income are not the same, of course. A business might have $10 million plus in assets, but only a tiny fraction of that in annual income. That applies to individuals too.

Judging from the other units of business the IRS’s Large Business and International Division monitors, the assumption is clearly that The Rich Squad is not going to be dealing primarily (if at all) with people who simply have a large Form 1040 and nothing more. That’s not their focus. In fact, there’s a reason The Rich Squad germinated in the fertile soil of the IRS’s Large Business and International Division.

They are adept at dealing with the complex business and investment entity structures that wealthy people so often use. For reasons of tax law, liability protection, hedging investment risk, anonymity, and succession planning, most wealthy people don’t put all their eggs in one basket. The Rich Squad audit, therefore, would logically take into account the range of assets and entities across the family group.

Most observers and practitioners suggest that this program is still in its startup phase. Yet of the details that have emerged so far, some are very clear. The written questions and paperwork required are extraordinary. See IRS High-Wealth Industry Group Evaluation of Wealth Squad IDR. The IRS commonly issues Information Document Requests, usually abbreviated to “IDRs” by tax professionals.

If you get an IRS IDR you are not required by law to respond. However, you should always respond. If you don’t, you will usually end up with a subpoena so it’s foolish not to consider them with care. Usually that means having tax professionals help you. In the case of a Rich Squad audit, that conclusion is even more obvious, and you should probably seek the assistance of tax attorneys rather than accountants since attorneys have the added benefit of attorney-client privilege.

Wherever you fit on the wealth scale, you should be aware that the IRS is doing more to troll for compliance glitches with wealthy taxpayers. You should also be aware that when it comes to wealthy people and the IRS, to quote Casablanca, “I think this is the beginning of a beautiful friendship.”

Leona Helmsley was already famous when she uttered the now immortal words: “Only the little people pay taxes.” Still, this ushered the Queen of Mean into the ranks of tax history in ways neither she nor the maid who reported the quip could have contemplated. Mrs. Mean would later achieve additional notoriety in the estate planning department with her $12 million bequest to her beloved dog, a Maltese named Trouble. See Helmsley’s Dog Gets $12 Million in Will.

The hotel baroness’ forays into tax planning were most famously of the sales tax and business versus personal variety. Nevertheless, her little people quote surely sums up what many people feel about the rich: their rules are different. The IRS may have taken a page from Mrs. Helmsley’s book in setting up its new Global High Wealth Industry Group. See ‘Audits From Hell’ Target Rich. Some now call this “The Wealth Squad,” but I like to call it “The Rich Squad.”

The Rich Squad is just getting started, but if you’re rich (more about what that might mean below), start getting your ducks in a row. Otherwise you too could end up with a Maltese named Trouble. Keep good documents and records, since if you ever have to go down this road much of the audit process will be providing copious copies of just about everything.

How Rich is Rich? This may be the question of the ages, right up there with the meaning of life, but no one seems to be saying just how rich you have to be to get targeted by The Rich Squad. Still, there are some figures available. The Rich Squad is part of the IRS’s Large Business and International Division.

That generally means more than $10 million in assets. Assets and income are not the same, of course. A business might have $10 million plus in assets, but only a tiny fraction of that in annual income. That applies to individuals too.

Judging from the other units of business the IRS’s Large Business and International Division monitors, the assumption is clearly that The Rich Squad is not going to be dealing primarily (if at all) with people who simply have a large Form 1040 and nothing more. That’s not their focus. In fact, there’s a reason The Rich Squad germinated in the fertile soil of the IRS’s Large Business and International Division.

They are adept at dealing with the complex business and investment entity structures that wealthy people so often use. For reasons of tax law, liability protection, hedging investment risk, anonymity, and succession planning, most wealthy people don’t put all their eggs in one basket. The Rich Squad audit, therefore, would logically take into account the range of assets and entities across the family group.

Most observers and practitioners suggest that this program is still in its startup phase. Yet of the details that have emerged so far, some are very clear. The written questions and paperwork required are extraordinary. See IRS High-Wealth Industry Group Evaluation of Wealth Squad IDR. The IRS commonly issues Information Document Requests, usually abbreviated to “IDRs” by tax professionals.

If you get an IRS IDR you are not required by law to respond. However, you should always respond. If you don’t, you will usually end up with a subpoena so it’s foolish not to consider them with care. Usually that means having tax professionals help you. In the case of a Rich Squad audit, that conclusion is even more obvious, and you should probably seek the assistance of tax attorneys rather than accountants since attorneys have the added benefit of attorney-client privilege.

Wherever you fit on the wealth scale, you should be aware that the IRS is doing more to troll for compliance glitches with wealthy taxpayers. You should also be aware that when it comes to wealthy people and the IRS, to quote Casablanca, “I think this is the beginning of a beautiful friendship.”

The onslaught of megaselling relationship books like Elizabeth Gilbert's "Committed: A Skeptic Makes Peace With Marriage," which sits at No. 9 on the New York Times nonfiction bestseller list for the week of Feb 19, and Lori Gottlieb's "Marry Him: The Case for Settling for Mr. Good Enough," which is at No. 18, might lead you to believe that female commitment-phobes and uberpicky daters are the modern obstacles to relationships and marriage.

Yet a 2007 poll by Meredith, a research and marketing company, found that 73% of women born between 1977 and 1989 place a high priority on marriage. That sounds right to me. It's an attitude that surfaced again and again in the interviews I conducted with young women for a book project on the long-term unmarried relationship. Unlike our boomer and hippie mothers who broke the rules of the '50s, my generation is marriage-minded. But society's messages to young women are so mixed that the path to that goal has been obscured and, at times, blocked. Those of us in our 20s and 30s know that dating—and getting into a relationship that leads to marriage—is at turns ambiguous, arduous, perplexing and often heartbreaking.

So why are "Marry Him" and "Committed" flying off the shelves? Because they do what all popular books on the subject have done over the years, decades and even centuries: They lay out rules, treating love, romance and relationships as if they are quantifiable and controllable. To be a young, single woman looking to settle down today is to be in the Wild West of dating history. Daters are ravenous for advice to order the chaos, even if it comes from a book, like "Marry Him," that berates them or, like "Committed," claims that marriage is a terrible institution for women (though the author gets hitched by her memoir's end).

"People are desperately looking for order out there because they want to be in committed relationships," says Jessica Massa, 26, who is developing WTFIsUpWithMyLoveLife.com, an interactive forum to help young people make sense of their relationships or absence thereof. "But the lack of signposts and guidance is making it very hard to get to the point where you end up in one."

You live together, but only until one of you gets a great job offer in London. You go out to dinner and a movie, but aren't even sure if it was an actual date. There is no longer that social urgency that pushes couples to the next stage.

The more pressing dating issue for young women today is not that they are skeptical about marriage or too choosy, but that their potential spouses are in less of a hurry to tie the knot than they are. A 2005 poll, "Coming of Age in America," which surveyed 18- to 24-year-olds, found that women had the edge on eagerness: 55% said they would like to be married in the next five years, compared with only 42% of men.

Adam Rich, 29, editor of Thrillist, a daily email blast targeting young men, says all this ambiguity is obscuring the traditional march to marriage and giving guys more leeway when it comes to casual dating. "This whole set of cliché indicators—call a girl to ask her out for drinks, then later a dinner date—are becoming less the dating norm. What if he Facebook messages her to meet at a wine bar where they share small plates? Where does that put them on the roadmap to the altar?"

Beth Bailey, the author of "From Front Porch to Back Seat: Courtship in Twentieth-Century America," thinks this might be an unprecedented time in the history of dating and courtship. "The lack of rules and structure in dating means it's become more difficult than it's ever been to get to the place where marriage seems like the obvious next step," she says.

Ms. Massa says that the many books on relationships that she has read "don't give me the lay of the land." Notes Mr. Rich: "If marriage is the destination, it's now increasingly unclear how one should put one foot in front of the other."

Just don't fault my generation for a lack of trying. Fault Ms. Gilbert, Ms. Gottlieb and their ilk—those who project their own neuroses on to the rest of us.

The onslaught of megaselling relationship books like Elizabeth Gilbert's "Committed: A Skeptic Makes Peace With Marriage," which sits at No. 9 on the New York Times nonfiction bestseller list for the week of Feb 19, and Lori Gottlieb's "Marry Him: The Case for Settling for Mr. Good Enough," which is at No. 18, might lead you to believe that female commitment-phobes and uberpicky daters are the modern obstacles to relationships and marriage.

Yet a 2007 poll by Meredith, a research and marketing company, found that 73% of women born between 1977 and 1989 place a high priority on marriage. That sounds right to me. It's an attitude that surfaced again and again in the interviews I conducted with young women for a book project on the long-term unmarried relationship. Unlike our boomer and hippie mothers who broke the rules of the '50s, my generation is marriage-minded. But society's messages to young women are so mixed that the path to that goal has been obscured and, at times, blocked. Those of us in our 20s and 30s know that dating—and getting into a relationship that leads to marriage—is at turns ambiguous, arduous, perplexing and often heartbreaking.

So why are "Marry Him" and "Committed" flying off the shelves? Because they do what all popular books on the subject have done over the years, decades and even centuries: They lay out rules, treating love, romance and relationships as if they are quantifiable and controllable. To be a young, single woman looking to settle down today is to be in the Wild West of dating history. Daters are ravenous for advice to order the chaos, even if it comes from a book, like "Marry Him," that berates them or, like "Committed," claims that marriage is a terrible institution for women (though the author gets hitched by her memoir's end).

"People are desperately looking for order out there because they want to be in committed relationships," says Jessica Massa, 26, who is developing WTFIsUpWithMyLoveLife.com, an interactive forum to help young people make sense of their relationships or absence thereof. "But the lack of signposts and guidance is making it very hard to get to the point where you end up in one."

You live together, but only until one of you gets a great job offer in London. You go out to dinner and a movie, but aren't even sure if it was an actual date. There is no longer that social urgency that pushes couples to the next stage.

The more pressing dating issue for young women today is not that they are skeptical about marriage or too choosy, but that their potential spouses are in less of a hurry to tie the knot than they are. A 2005 poll, "Coming of Age in America," which surveyed 18- to 24-year-olds, found that women had the edge on eagerness: 55% said they would like to be married in the next five years, compared with only 42% of men.

Adam Rich, 29, editor of Thrillist, a daily email blast targeting young men, says all this ambiguity is obscuring the traditional march to marriage and giving guys more leeway when it comes to casual dating. "This whole set of cliché indicators—call a girl to ask her out for drinks, then later a dinner date—are becoming less the dating norm. What if he Facebook messages her to meet at a wine bar where they share small plates? Where does that put them on the roadmap to the altar?"

Beth Bailey, the author of "From Front Porch to Back Seat: Courtship in Twentieth-Century America," thinks this might be an unprecedented time in the history of dating and courtship. "The lack of rules and structure in dating means it's become more difficult than it's ever been to get to the place where marriage seems like the obvious next step," she says.

Ms. Massa says that the many books on relationships that she has read "don't give me the lay of the land." Notes Mr. Rich: "If marriage is the destination, it's now increasingly unclear how one should put one foot in front of the other."

Just don't fault my generation for a lack of trying. Fault Ms. Gilbert, Ms. Gottlieb and their ilk—those who project their own neuroses on to the rest of us.