When Jeff Huening realized that upcoming repairs on his 1992 Toyota Paseo would likely exceed half its blue book value, he knew it was time to begin shopping for another car.

Since the Paseo had been a gift from his parents, Jeff decided to treat himself with his first car purchase. He began visiting dealerships and test-driving various entry-level luxury models in the $30,000 range, such as the BMW 325, Lexus IS 250, Infiniti G35 and Acura TL.

However, Jeff couldn't get around the fact that "a new car depreciates the moment you drive it off the lot."

"I decided that if I bought a slightly used car, I could get the model I truly desired and let the original owner eat the new car depreciation," says Jeff, 30, of Chicago.

And what he really wanted was a Porsche. Research soon revealed that for the amount he was willing to pay for a new entry-level model, he could buy a used Porsche Boxster convertible with low mileage.

His research didn't end there. Jeff visited a Porsche dealership to gain first-hand information about the car from a salesperson. "He cleared up a lot of misconceptions I had about the cost of ownership, safety and reliability," he says.

Jeff also test-drove a new model, even though the $45,000 plus price tag was well beyond his already-established budget. Before leaving, he told the salesman the price, color and features he was looking in a used car.

In the meantime, Jeff called his insurance company for a quote, and was surprised -- and relieved -- to learn that rates were comparable to his Toyota's.

He also visited Porsche-related Web sites to find out about hidden pitfalls of ownership from current owners. After learning about common problems and repair costs, he decided a warranty was in order, even if it meant paying more.

Within two months, the Porsche dealership called with a used model fitting Jeff's specifications on site, a 2002 blue Porsche Boxster convertible with only 6,800 miles.

"I bought the car as 'certified used,' which did add to the purchase price," he says. "The car had gone through a detailed inspection and re-conditioning by a factory-trained technician and looked like brand new to me. It also came with an extensive two-year warranty, which added to peace of mind."

Two months later, Jeff has no regrets about his luxury ride.

"Friends love getting a ride and valets at hotels and restaurants always leave it right out front," he adds.

He offers this advice to others who are considering buying a used car:

• Know what's a fair price. Jeff used reports from Kelley Blue Book, Edmunds.com and Consumer Reports to negotiate $800 off the dealer's asking price. "Also, I went to buy the car on the last day of the month, which the salesman revealed created urgency in him to sell the car so he could meet his sales goals."
• Be prepared for related costs. While Jeff parked his Paseo on the street, he decided to lease a garage spot for the Porsche. He also budgeted in an extra $1,000 each year to have the high performance tires swapped for snow tires each winter.
• Be flexible. A global positioning system was on Jeff's original wish list but decided it was something he could live without when the dealer called about his car. "Buying a used car, you have to be flexible," he says. "It's virtually impossible to get the car exactly as you want it."

By Darci Smith

Interest.com Contributing Editor

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