Used Car $22,000 range

2001 Porsche Carrera Coupe (Too old, monstrous repair bills, oil changes run approx $90+ each)
2008 BMW 128i Coupe (Car for a woman....seriously.....although, easily the most fun to drive of anything listed)
2006 Mercedes-Benz CLK500 Coupe - (This car is a Yes - but again, with the repair costs if no extended warranty is offered, will hurt you in a big way)
2008 Chevrolet Corvette (no backseat) - (Great American gearhead car, but women (and men, alike) have a pre-conceived notion about a young dude in a 'Vette, much the same way you have one of an old dude in a 'Vette)
2010 Hyundai Genesis Coupe - (My pick. While people are still holding some bias against the "Hyundai and KIA's" of the world, there is no denying that they are coming out with some really great cars. This one will be reliable, decent on gas, look good, and probably give you the least problems of everything listed)
2005 Nissan 350Z (no backseat) - (Asking for a headache, but the most fun if you like to tinker under the hood)
2008 Chrysler Crossfire (no backseat) - (Underpowered and not worth your time. Chrysler had the opportunity for a home-run here and they made the powertrain wimpy and castrated. Dud.)
2007 Saturn Sky (no backseat) - (Not a car for a 27 year old guy trying to pick up girls.....at all)

Just make sure you get a silver one.

Since you are 27 you might want to consider a sedan. You should finally grow up in the next few years. That's about the time I started to, I'm still fighting it though. I just sold a 528i that my son is crying about. They will pull tail.

Quote from Kjelstad : Just make sure you get a silver one. Since you are 27 you might want to consider a sedan. You should finally grow up in the next few years. That's about the time I started to, I'm still fighting it though. I just sold a 528i that my son is crying about. They will pull tail.

Listen to this man.
27 was about the age for myself as well.
I ended up with a BMW sedan, then an Audi sedan.
Both outstanding cars that make girls quite happy to get into.
These days, I drive a Mazda CX-7 SUV (silver, haha) and not a single chick looks.
But.....now that I have a wife, this is less of a concern.

Gearhead here.... My honest opinion? With so few miles every year, now is the best time for you to go out and lease something (again). Used car values are at an all time high, which causes lease rates to go down. Pick out something that you want and go talk to the dealership, and negotiate a lease contract based on your usage.

If you want to actually buy something.. forget the Germans, they'll ruin you financially. CPO Infiniti G37 will give you most of the kicks of BMW ownership without the astronomical cost of it.

all good points, i have the same concerns on all of those cars Evo - i needed some validation on a few (Vette)

i'm leaning towards the Benz CLK's, right now i could get a 2007 CLK550....the engine is faster than the 03 CLK55 AMG

TXBoltsFan - i like the infinity's but my brother has one and they'e all over the roads... too cookie cutter for me

1. Be careful of insurance costs as well - some of those cars will be much more to insure than others
2. I also say steer clear of the Germans if you're buying - maintenance cost will kill you. Lease if you want a German car.
3. You might consider a lease on a 370Z - depending on where you are, might not be much different monthly than a 22k loan.

Time to grow up and get a boring sedan or cross over. I would get a FJ Cruiser to keep some man hood. When I was 25 I bought a brand new 2005 Saab 93 convertible (hence user name)... Loved that car. 6 years later a proud owner of a 2011 Camry LE but I got gramp's 1929 Model A and a 1953 F100 in the shed.

Wow, I voted for the Hyundai. I did not expect that to be such a front runner. Hyundai really stepped it up the past few years. Who would have thought that they would pass up American cars in the style department. Come on FORD, GM, etc. Let's make some good looking cars. I WANT TO BUY AMERICAN