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Diamonds: an investor’s worst enemy (access required)

Dear Mr. Berko: I'm a 35-year-old physician, and I'm finally getting married. A jeweler in Chicago has shown me a nearly flawless, $58,000, 5-carat diamond for my fiance’. It's a wonder to look at and seems like it could be a good investment. When I asked the jeweler how much this stone could be worth in 10 years, he couldn't answer me. So I'm putting this question to you. – WS, Chicago

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Don’t spend that escrow windfall (access required)

DEAR BENNY: We moved to Jacksonville, Fla., in 2010, but still own a home in Pensacola that we are renting to some friends. We got a check in the mail for an alleged overpayment from escrow. I remember telling my wife they had the home insurance wrong on the HUD-1 form, so we figured it was discovered and they reimbursed us. So we used the money to pay bills.

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3 techs and 1 eatery might double your shares (access required)

Dear Mr. Berko: I have a little over $12,000, and I would like to speculate with it and buy one of two stocks that trade below $10 a share. Please recommend a few low-price issues that can maybe double their value in two or three years. I don't want to lose this money, but I'm willing to take a chance if there's a possibility that I can double my money. – TJ, Rochester, Minn.

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Get rid of an uspide-down second home (access required)

DEAR BENNY: We live in California and own a second home within five miles of our primary residence. This second home has been used as a rental, initially to persons we were not connected with in any way. For the past 10 years, two different sets of relatives who were in need of a new start in life lived in the home.

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