During the most fruitful economic times, when the rich appear to get endlessly richer, it is almost impossible for the average American to relate to the wealthy, and vice versa. But when things go bad-and right now the economy appears to be pretty darn bad-attitudes change. It's not that the average American can suddenly relate to the wealthy, or that the wealthy somehow share the uncertainty of the average American. It's just that the financial strain begins to spread across all income levels. Sure, the degrees of pressure will be different, depending on one's personal wealth, and it's hard to worry overmuch about an individual who's struggling because his or her multimillion-dollar portfolio happens to be illiquid. But during today's sluggish recovery from a deep economic recession, the simple fact is that fewer Americans, even the rich ones, are immune to financial stress.

When we zero in on wealthy Americans we find that, just as with the mass affluent, the baby boomers face the biggest challenges. The boomers are in a unique position: They have children, parents, jobs, businesses, houses and other obligations that demand significant care and investment-and sooner rather than later they are entering retirement. Their plates are brimming with planning needs. So what are wealthy boomers most concerned about? Frankly, it's many of the same things middle-class boomers are concerned about: the value of their homes, the possible impact of rising taxes, the cost of their children's education and the remains of their retirement portfolios.

Of course when confronting financial challenges, there is one significant factor that separates the most affluent boomers from those lower down on the income ladder: "These are all people who are still in good shape," says Ross Levin, founding principal and president of Accredited Investors in Edina, Minn. "So the stress is relative."

Housing-Who Will Buy?

Much of the media coverage surrounding the collapse of the real estate bubble focused on people who bought homes they couldn't afford. And for good reason: Many parts of the country, especially Arizona, California, Florida and Nevada, are littered with foreclosed homes that never should have been bought or built.

But there is another, less-reported story that came out of the American real estate bubble. Wealthy people, seeing home values rise, began buying up second and third homes as investments-and now, in this down market, they are stuck with them. Worse, some wealthy clients, now empty nesters, are stuck in large primary residences when they'd rather downsize. The next generation is not ready, willing or able to trade up, if they can buy a house at all.

Todd Clarke, president of CLS Investments in Omaha, Neb., says the real estate market has served boomers a rude awakening. "They had their McMansions which they thought were worth a lot of money, and they've seen the prices plummet 25% and 50%," he says. "It's caused them to take a deep breath because the game has changed."

Levin works with a couple that owns a nice big home in Minneapolis but has reached a point in life where they don't want to maintain three stories and 8,500 square feet. Instead, they want to move to a 2,000-square-foot condo on the river. Unfortunately, the value of their house has dropped by about 30% in the last three years, and they don't want to sell-the price feels too little. "To sell the home and buy the condo is financially neutral," Levin says. The problem is emotional, not economic: "They feel like their home should be worth more than the condo."

Another of Levin's clients bought a second home in Florida before he sold his first home there. Now he can't sell either property. Worse, these properties are in addition to his primary residence in Minnesota. Another client of Levin's put a $100,000 down payment on a $500,000 Florida condo right before the crisis hit. Levin's firm advised the client to walk away from deal even though he would forfeit the down payment. "Looking at [Florida condos] three years later, I think he's way better off having done that," Levin says.

For clients with second or third homes that are expensive to maintain and being used a lot less than planned, Levin does a cost analysis: He compares the cost of keeping these homes versus selling them at a reduced price or even a loss. The bigger problem for a lot of second-home owners is the lack of new buyers. "Unless the next generation of buyers sees a lot of opportunity and upside, they're much better off renting a place for the summer," he says.