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I'm looking to reward myself with an entry-level luxury sedan. I'm considering the options from BMW, Mercedes, Audi, Infiniti, Acura and Lexus. I love getting deals and this would be no different. I'm looking at new versus used, purchase versus lease. I have a short commute and, on average, only put 15,000 kilometres per year on my vehicle. What would be the most savvy purchase? – Chris

Leeder: As mid-life crises go, I'd say this is a fine and well-calculated reward, Chris. Is there no part of you that just wants to snap up something shiny and powerful without doing the math on the deal, though? All this calculating! Nonetheless. We shall persevere.

Richardson: I went to school with people like Chris. Kinda nerdy, kinda quiet. Now they're all buying luxury cars because they were careful with their money. I can't say I'm not a little envious. The new versus used decision is a personal thing, though.

If you want the latest and safest, then new is the only way to go, obviously, but you pay for it: a regular new car drops 20 per cent in value as soon as it leaves the dealer lot, and about a third over the next two or three years; a premium car often halves in value before you're ready to sell it.

There are great deals to be found on used Bimmers and Benzes – this is because they're costly to maintain and their warranties are starting to run out. Find a good one and you'll be in love, but you'll regret a poor one for as long as you own it.

Leeder: Given the low number of kilometres Chris drives, leasing might be a great option for him. In the simplest of terms, leasing is a way to get more car for less money. Sure, you've got to give the car back at the end of your lease term, but you've basically just paid for the value the car lost during the time you drove it (under a full warranty, I might add). You're out of pocket for what you shelled out for the down- and monthly payments, but not for the value of the whole $60,000 kit and caboodle.

And you have a choice: buy out the car for its residual value (boo) or lease another brand new one (woo hoo!). It's a good option for those who have an appetite for cars that hold their value and like to have something new-ish in the driveway – and for Chris, who will be rewarded with lower monthly payments if he isn't going to drive more than 15,000 kilometres per year.

Richardson: Leasing isn't a bad option for a premium car, but you have to think of it as a long-term rental: you're just paying for the right to drive it for the duration of the contract. There are often tax savings, especially if it's considered a business-use vehicle, but you don't own it, and you have no collateral with it.

You pay roughly half the cost of the vehicle over the time you have it, but you must give it back or buy it at a pre-determined price at the end of the contract. Borrowing costs are currently so low, though, that about three-quarters of Canadian buyers prefer to bite the bullet and actually own something after six or seven years, but the beauty of leasing is that you get to drive a new car that's always under warranty. That's a good thing with a premium high-tech car.

Leeder: So we agree on lease. Let's talk cars. I'm striking Acura off the list. No crisis cars there right now. I'm also deleting convertibles because we can get you more car without the premium you'd pay for one.

You should go test drive BMW's 435i coupe, which has 300 horsepower and comes with a six-speed manual if you want it (there's a cheaper, less-powerful 428i, too). Infiniti's new Q60 coupe should also be on your list – it's a dream to drive. And if you want true entry level, you could consider Audi's A4, which you can buy with 'S' level trim, meaning you get fancy wheels and sportier styling for a lower price.

Richardson: All kinds of options here, but you've got to make that new/used and buy/lease decision first. When that's done, go for a drive in each of the car's Jessica's suggesting – and forget the 435i – you'll be just as happy and wealthier in the 428i. Don't forget Lexus and Volvo. When you've narrowed it down to three or four, send us another note and we'll set you straight.

Having trouble deciding what new car is the best fit for you? E-mail, placing "What Car" in the subject area.

Matt Bubbers drives the new Volkswagen Alltrack, an all-wheel-drive wagon that can take you everywhere an SUV can.

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