2006 Mercedes-Benz S500

The W220 Mercedes-Benz S-Class gets a pretty bad rap in the grand scheme of things, and mostly rightfully so. What replaced the W140 chassis was a stark departure from the bank vault-like feel and stately styling, and went into deep into soft lines and subpar materials. It harsher words, it was a blob. It wasn’t until the facelift compare around that the W220 really became a little bit more friendly on the eyes. In additional to the S55 and S65, you could also option the AMG bodywork and wheels on the S500 to give it a little more flash. Today’s car, a 2006 S500 up for in Florida, is exactly that. You might have noticed the color too.

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2006 Porsche Cayman S

Green and brown is like chocolate and peanut butter to me. Smooth all the way. If I ever went the route of actually spec’ing a car from new, it would be a nice dark green, over some kind of tan of brown leather. I’m sure I’m not alone in this, so when this 2006 Porsche Cayman S popped up for sale, I naturally had to take a closer look. Forest Green Metallic over Special Cocoa Leather. Yes, please. However, once I started taking that closer look, it didn’t seem so lovely anymore. Let me explain.

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2006 Maybach 57 S

I promise this is the last Maybach for a while. I also promise this one is worth it. This the 57 S. The standard wheelbase car, if you could call this thing standard, but with a 6.0-liter M285 twin-turbo V12 in place of the same M285 as we get on the 57, but with an extra half a liter. It also rides a half inch lower and was standard on 20″ wheels. Maybach says the S stands for Special, I always looked at it as Sport, but you can make your own call. Of course it was ungodly expensive at over $370,000, and now it is literally worth a fraction of that. However, if you were expecting the normal Maybach interior of boring beige leather and a bunch of fake wood, you would be wrong. Very wrong.

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2006 Porsche 911 Carrera S Club Coupe

One of the more interesting special editions to come out of Porsche in the last 20 years was the 2006 911 Carrera S Club Coupe. As a thank you to PCA members, or maybe a way to milk some more money (probably both), Porsche produced 50 Club Coupes only available to PCA members though a random drawing of everyone who put their name in the hat. If they were chosen, of course they still had to pay $105,000 for a Carrera S painted in exclusive Azzurro California and with a bunch of options. For comparison, a 2007 911 Turbo was around a $120,000 at the time, so this was not a cheap C2S. Seems like a bad deal, right? Well, not if you held on to it for all these years.

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2006 BMW 550i

While there wasn’t much of a contest between the E28 M5 and E34 535i, by the end of the E34 run the 540i M Sport was – for all intents and purposes – a M5 without the S38. BMW upped the ante to 400 horsepower in the new E39 M5, once again widening the gap to the 540i model. But the successor E60 545i offered 330 horsepower with matching torque in 2003 alongside the outgoing E39 and once again the gap in performance became much smaller. That gap was made almost impercievable in 2005, when BMW revised the E60 with the increased displacement in the N62 motor. Now sporting 4.8 liters from the N62B48, the new “550i” now had 360 horsepower and 361 lb.ft of torque – a much better match for the S62. What was perhaps more amazing was that the new N62 also nearly matched the torque of the new E60 M5’s S85 V10. But while that screaming V10 produced far more horsepower, the peak torque was reached only at 6,100 revolutions – hardly practical in your daily commute. In comparison, peak twist on the N62 came at a much more realistic 3,400 r.p.m.s, and on the fly these 550is were – and still are – seriously quick sedans. They also introduced the next generation of design language and computer technology into the 5-series. Some love the look while others lambaste the design. While it’s certainly not my favorite 5, at least it’s distinctive and different in a world full of cookie-cutter designs and dare I say I think it may look better today than it did new – perhaps a testament to its avant garde lines. While the lust-worthy V10 captures the imagination of enthusiasts, day to day the 550i is likely as fast 95% of the time and much cheaper to get into and run. The thing is, is this the one to get?

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2006 Porsche 911 Carrera

The 997.1 Porsche 911 is probably my favorite “budget” 911. I wish I could put “budget” in size 82 font quotation marks given we are talking Porsche here, but in the grand scheme of things where a new base 992 C2 is $100,000, your buck doesn’t go very far these days. Now you are probably saying, “What about the 996?” And yes, you are right. But given the very small price difference between the 996 and 997.1, I think it is the perfect sweet spot of having a modern 911 without spending over $50,000 just to get a seat at the table. Today’s 997 has my favorite Lobster Fork wheels and isn’t a boring color. There’s only one problem though – the transmission.

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2006 Mercedes-Benz E350 Estate

Your dollar doesn’t go very far if you want a Mercedes-Benz station wagon. I’ve expanded on the value of the wagons in the past, and that seems to be holding true in almost every example. However, if you really want a long body with a three-pointed star, you can find a good buy if you search hard enough or adjust your standards low enough. This 2006 E350 Wagon up for sale Tennessee is a little bit of both.

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2006 Porsche Cayman S

The magical $20,000 mark doesn’t buy you much Porsche. Even less when you are talking about a Porsche with an engine mounted somewhere behind the seats. You have the 914 and the Boxster, and maybe an R-title automatic 996. However, now as the years pass, we have another option. I know I already ruined the surprise, but the 987 Cayman is suddenly under the $20,000 and there are lots of them. Granted, a lot of them are the not-so powerful base Cayman with the 2.7L, but to my surprise, this is a Cayman S!

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2006 Porsche 911 Carrera S

In terms of value in the Porsche 911 world, where the “value” is a little bit of misnomer, I personally think the 997 is in a wonderful spot. You have a respectable amount of safety and performance, the unmistakable looks of a 911, all while not needing a six-figure income to buy or maintain. Yes, some of the more special 997s still bring huge prices, but for the more common 997s, its one of those or a new Honda Accord. The early Carrera and Carrera S cars are particularly appealing to me, especially when equipped with the 19″ lobster claw wheels. As luck would have it, this is what we have today in this 2006 Carrera S up for sale in California. The thing is, it isn’t equipped with the traditional six-speed manual transaxle, but rather the last of its kind five-speed automatic. Is this a deal breaker?

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2006 Mercedes-Benz E500 Estate

Station wagon, estate, avant, whatever you want to call them, they are still popular. How did I come to that conclusion? Well, take a look at basically any German vehicle that is offered in both sedan and wagon and you’ll see that the wagon transacts at a higher price tag on the used market. This is especially true when it comes to high performance models like an Audi RS or AMG. A lot of that has to do with having your cake and eating it too, along with the exclusivity, as high performance wagons are made in extremely small numbers. However, even in standard base models, the wagons are still bringing premiums over sedans. Today’s car, a 2006 E500 Estate up for sale in California, follows that trend. Who says wagons are uncool?

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