[Porsche-O-Phile]

Never.

Leasing is for suckers and new cars are for even bigger suckers. Maybe if I win the lottery or similarly end up in a situation where I have money to blow I'd consider it, but to dump that much money into a rapidly-depreciating item is even more financially suicidal than "investing" in the current housing market, IMHO.

My car payments are exactly zero. They've been this way for a long time (my last one was for my motorcycle, which only cost me about $150 a month to finance - paid off a while back and still running great). I own three Porsches and a bike for way less than the total purchase price of a Toyota Camry. I can carry liability-only insurance and avoid getting ripped off by the insurance companies. I have THREE spares in case something breaks to still get to work without a problem. And if I ever fell on financially hard times I could liquidate two or even three of them with virtually no loss (only what I put into them in terms of time upgrades and basic maintenance).

Sorry, but I think I'm laughing all the way to the bank on this one.

Even a modest piece-of-crap econobox is going to cost you in the neighborhood of $300-a-month - probably closer to $400-a-month if you factor in the ripoff insurance you're required to carry. Let's say it's $350 for sake of arguement. Over the course of a year that's $350 x 12 = $3,600. I can tell you I spent probably around half that on required maintenance items for my entire fleet last year. Now granted I spent a lot more on upgrades and other "non-essential" work, but I don't consider that, since one might opt to similarly spend on another vehicle - new or otherwise. It's discretionary.