I spotted this 1990 Mercedes-Benz 560SEC on my local Craigslist and it got me thinking.  While this car would make a good entry to a prominent auto blog’s daily feature about interesting cars for sale, I’m less interested in whether their commenters would rather spend the $15k on importing a South African Golf MK2 with a European diesel and an AWD swap and more on whether you can make a case for buying a classic like this one instead of an equally expensive brand new car. Say you have $15,000 to spend on a new car, and you’re between a 1990 Mercedes-Benz 560SEC and one of the entry level new cars available right now, which do you buy? (This might seem like a manufactured dilemma, but most car guys I know have asked themselves questions just like this.)

The $15,000 asking price the owner wants for this 1990 Mercedes 560SEC is very close to the $16,400 NADA says is the high retail price on these cars, but nowhere near the $81,500 it cost new (somewhere around $130,000 inflation-adjusted to today’s value). There aren’t many cars available right now for under a $15,000 starting price. Seven, in fact, including the niche Smart Car. Even if you checked off enough luxury features boxes to match the Benz’s, you’d end up with a poor imitation of luxury, like a Channel purse from the flea market. You’re getting a lot of car for your dollar when you buy one older than some of the folks you’ll see out at the bar tonight (and a lot older in the case of the more laissez-faire bars).

The good: depreciation on a 22 year old luxury car hit during the Clinton era, so if you do need to get rid of the car, you can expect somewhere near what you paid for it, assuming you don’t drop the $30,000. The attention you’ll get in this car will be off the charts. Enthusiasts, even BMW fanatics, will all appreciate the active decision you made to keep an automotive icon on the road. If you’re trying to court the ladies, a car with this much style and comfort without the pretention of a modern luxury car is hard to find (if you’re a lady, take it from me, any girl in a sports car that doesn’t consider a Civic coupe a sporty car is a dude magnet). You’ll never find a car with this level of style, luxury, build quality or performance new for $15,000. Mercedes products, especially from this era, are also notoriously reliable. If you look around your local farmer’s markets and college campuses, you’ll probably spot one. I had a friend in college who got one for his first car and had been trying to kill it ever since by way of normal (read: non Top gear) abuse. Last I heard it was still kicking.

The bad: Upkeep costs. Even if the car has been gone over with a fine-toothed comb, and an hour or two with a qualified mechanic will confirm the seller’s assertions that it has, parts wear out over time. The alternator will go eventually, and even that, which is an easy fix on a 10 year old Civic, can be an expensive proposition on a high end car (a friend with a late model SL recently paid $2,000 for an alternator replacement) and while the W126 is much less overcomplicated than newer Mercedes cars, it’s still not an aircooled Beetle. The other issue with upkeep is finding parts. While the W126 was a popular car and was sold for a long time, once again it isn’t an aircooled Beetle, so you might find yourself with a broken part and no aftermarket or OEM replacement available. At that point you’ll find yourself in contact with very good mechanics, junkyards and enthusiast forums to keep it running. If you’re considering a carbureted small block Chevy swap, you’ve passed the point where the car is a viable daily driver. If you don’t have cash in hand, you’re going to have to find a classic car specific lender to finance this, so you’ll probably need a more sizeable down payment and end up with a higher interest rate than an incentivized$15k commuter car.

Time to return to the first paragraph and my answer to the question: Buy the Benz, it will probably go almost as long as a new car without needing major repairs if it’s in good shape and if it doesn’t the resale value for one with a blown motor or transmission is much higher than a five year old economy car. Plus you’ll make enough friends with it that you’ll be able to get a ride to work when it’s in the shop.

Images via Craigslist ad, hopefully the seller doesn’t mind and this will get him some extra publicity for his gorgeous car.