He's worked hard for every dime. Can his money work for him now?

Stretched too thin, real estate investor shifts his strategy

On paper Daniel Atanasov, 32, looks like a young Donald Trump.

Atanasov bought a three-family house in East Boston in 1999 that has appreciated handsomely. Two years ago he snapped up another triple-decker in Winthrop for $460,000 and is the midst of renovating that. Last spring, he and his brother bought land on the Florida Gulf Coast, intending to flip it for a profit in 2006 and use the proceeds to buy a vacation place for the family. Then a three-bedroom condo in Bradenton, Fla., caught his eye, and Atanasov bought that too.

His net worth is approaching $800,000. So what's his problem? Atanasov's spending spree has left him with five loans to pay back totaling about $6,250 a month. He also has to contend with utility bills on his properties, renovation costs for the Winthrop triple-decker, and a car loan.

''I've stretched myself very thin and would like some help on what to do with the East Boston or Winthrop properties," said Atanasov who volunteered for a Boston Globe Money Makeover. ''I would like to hold onto them until I buy a single-family home, but it is becoming apparent that one of them needs to be sold."

Historically low mortgage rates and rising prices have made real estate a popular investment. Nationally, 23 percent of all houses bought in 2004 were for investment, according to the National Association of Realtors. And median home prices in Massachusetts alone have appreciated more than 25 percent over the past three years, according to the Massachusetts Association of Realtors.

But now a slowdown is apparent with more homes sitting on the market longer, forcing some sellers to reduce prices. That scenario has left some investors wondering whether it's time to sell, but not Atanasov. ''For me it is just the opposite. As prices go down I think it's a good time to buy another piece of property," he said.

Besides optimism, the other ingredient to Atanasov's paper wealth is hard work. This young accountant, whose salary is $65,000 a year, has sweated for every penny. The son of Yugoslavian immigrants, Atanasov began working at age 14 with his father, who is a plumber. Later, he won a scholarship to Boston College, where he played soccer. Upon graduation, he secured a job and plowed money into the bank by living with his parents for six years, leaving the area briefly to play professional soccer in Greece.

He bought the East Boston house at auction for a mere $110,000 and worked nights and weekends with his father to fix it up. The backbreaking renovation included excavating a basement with a pick and jackhammer and carting away the debris in a wheelbarrow. He now lives on the second floor of the Winthrop house, without electricity, as he finishes the top apartment. And Atanasov still does weekend plumbing jobs with his dad.

''I'm basically working seven days a week," he said. ''I just love to work."

''You have so earned everything you have. There is no luck involved at all," said fee-only financial adviser Susan Kaplan, president of Kaplan Financial Services in Newton. ''Your hard, hard, hard, work has catapulted you to a place that people twice your age have not reached."

But Atanasov's big mistake, she said, is straying from what made him successful -- buying undervalued properties, fixing them himself, and then renting out the units.

The conscientious Atanasov, for example, failed to read the fine print on the Florida condominium. Buried in the 200-plus pages of condo documents was the stipulation that the condo can not be rented in less than six-month blocks.

''When you think about the Florida place, it was not undervalued: It was all new, and you can't rent it," Kaplan said.

Her advice: Dump the Florida properties and hang on to Boston. The Winthrop house can't be sold anyway until it's fixed up, and Atanasov can't afford to finish it while he's carrying his Florida real estate. Sell Florida and use the extra cash to pay for the Winthrop renovation.

The East Boston house should not be sold because it is ''such a cash cow," Kaplan said. Valued at more than $600,000 today, the property earns about $1,200 a month.

She also strongly advised against turning the East Boston place into condominiums until he is ready to sell. Converting to condos would cost at least $10,000 in legal and architectural fees for the documents, cause the property to be reappraised, and pose a huge tax liability when the units were sold.

Alan Pasnik, an analyst for the Warren Group, a Boston firm that publishes real estate market data, agrees with Kaplan that Atanasov would be foolish to part with the Boston properties. Three-family houses in undervalued neighborhoods are good buys, he says, as evidenced by the increase in the median price. In East Boston, the median price has roughly doubled since 2000, from $222,000 to $485,000 in 2004. Over the two years Atanasov has owned his Winthrop house, the median price for three-family houses there has increased from $372,500 to $551,500.

''Tell him to buy more if he can afford it," Pasnik said. But he also cautioned that Atanasov should diversify his investments, making real estate only a part of his portfolio.

Kaplan was already on that, chastising Atanasov for not contributing to a 401(k) because his employer didn't match contributions. More surprising was a final recommendation from Kaplan that the soon-to-be married real estate investor draft a prenuptial agreement with his fiancée, Judy, a school psychologist in Duxbury.

When asked if that wasn't a bit unsettling for a young couple in love, especially when the tycoon in question is not exactly Donald Trump, Kaplan didn't blink.

''It's jarring only when people think of divorce. But let's think of death. What if, God forbid, something happened to them right after the wedding. Would it be fair that another family inherit the property that Dan's family worked so hard on?"

Atanasov appreciated the wisdom of the advice. Reached a couple weeks later, he had listed the Florida condominium, was contributing to his 401(k), and was expecting a draft of the prenup from the lawyer any day.

To be considered for a Money Makeover, fill out the form at the ''Your Money" section of www.boston.com/business, or call 617-929-2916 and ask for an application.