Agree with Denis, Jetta TDI or Mazda ...... Maybe not luxury, but a great driving experience.

Can you find a late model Cadillac CTS for < $20k?

Throw in another vote for the Mazda line up

I'd look for a 2006-2008 Acura TL Type-S. Test drove one a couple of years ago and it was very nice, and also fast. I should have bought one instead of my RSX Type-S, but I'm not a 4 door kind of guy.

Yes, you can get a 2008-2009 CTS with 50-65K miles for under $20K

IMO, this would be an excellent choice to meet all of the OP's requirements stated in post #1.

Hmm I actually own this car. It's fun (zoom zoom) and I get 32 mpg on the highway when I drive it soft, but it also handles extremely well.

It has 4 doors, gets good gas mileage and you should be able to find a 2008-2009 well below your price range. It's the smaller body style and much easier on the eyes.

Excellent advice. I have a company car (I own the company) and decided on a new Toyota Venza three or so years ago...it is a complete Milquetoast auto but it has all the things I wanted in a company car: plenty of storage capacity for luggage, great a/c, sat radio, good in city traffic, easy to park, etc. 60K miles later and all is well.

In my line of work I deal with a lot of civil servants and military, often taking them places in the Venza, etc. I have seen other business owners make the mistake of having too nice a car: Some of the GS folks and military are NOT car folks and think a luxury car is silly and that it reflects poorly on the owner of the car.

I don't agree at all, but know your audience.

Also, in certain parts of the country a "foreign car" is not a positive.

Given the OP's location, I would not recommend a 6 unless he's cool with having rust issues in a couple years time.
At least that's been the experience with the 3 in our family, and the 6s of a couple extended family members in the Chicago area.
Great cars otherwise...

+1

Lots of interesting input and advice so far. I will have to respond in detail tonight when I am on my computer.

When I bought my E39, I was looking hard at a Mazda 6 as well. It was a few years newer and had a few less miles, but was also a couple thousand more expensive. And after driving the cars back to back, it just really didn't compare.

As I said in my initial post, I know what the logical move is, i just have to decide if I want to be logical. It would be interesting to hear from any owners of some of the suggested cars about what type of $$ go into them from about 90k miles to 150k miles. Having had BMW's since 1993, I know what to expect there, for better or worse.

This would be my list:

Mazdaspeed 3
Mazdaspeed 6
GTi
GLI
Pontiac G8 (360 HP auto GT or 402 HP 6-speed GXP)
Audi A4
BMW per prior comments
Volvo S60R
Saab 9-5 Aero (you can steal these right now)
Mazda RX8 (does it count as a four door?):)
Chrysler 300 SRT-8
Dodge Charger SRT-8
Subaru WRX/WRX STi
Mitsubishi Lancer Evolution
Subaru Legacy GT - grown up STi

That's just a quick dump of my brain, cars that have four doors and should be $20k or less. Obviously it runs the variety gamut. I included the WRX and Evo, but suspect that you'll find the interior to be cheap compared to your BMW. The Legacy as well as the Mazdas have a much more upmarket interior than the WRX/Evo.

This is the best advice. If you're in sales and the clients are going to see your car, (or even worse, ride in it), make the image issue the #1 concern. Find the most tolerable solution that makes the right image. Late-model, nice but not too nice, quiet and bland is best. Even the color should be attractive but not attention-seeking.

For non-car people, all they look at is the age of the car and if they think it's silly or reflects immaturity. :cool:

If you're struggling with the logical versus emotional, I find the best thing to do (when it comes to cars) is put a price tag on it. Know what it costs to follow your heart. Sometimes you'll be surprised at how little it costs, sometimes how much.

Here's what I would recommend (purely logical) to a client in your situation:

Buy a long-term-rental return 2011 Nissan Altima 2.5S from Hertz or Avis business logistics in Chicago. I can buy a nice one with ~36-40K miles for about $13K, delivered. They typically have new tires by that point. They're very nice cars and a lot more fun to drive than most in that class.

Take out a 48 month loan for $10K at 3%. You'd have a $220 monthly payment. I know you can afford more, that's not the point.

According to official EPA ratings, 30,000 miles per year of 70% freeway driving calculates to a $3,850 annual ($320/mo) fuel cost at $3.60 gallon regular gasoline. Compare this to the $5,500 annual ($460/mo) fuel cost of your current 530i using premium (as BMW requires) at $3.85/gal. That means you'd be saving $140/mo in fuel.

Three years from now, May 2015, you'll sell the car with 128K miles for $6,500 as some kid's graduation present (this isn't a WAG, this is pretty accurate). You'll still owe about $3,300, so you're basically recovering the money you're now injecting as a down payment.

Then do it again.

Meanwhile, you're saving money compared to what you *think* you'd like to do ($20K 2008 328i with 55K miles?) in terms of interest, fuel, insurance, repairs, maintenance, and depreciation. Put that money towards a fun hobby car that you can enjoy on weekends and playdays (or date nights). Even if it means taking out a loan, remember you're saving $125/mo in fuel compared to where you're at right now. Maybe even saving in payment -- how much more than $220/mo are you paying now?

OR

Follow your heart and get what you want, keeping in mind the opportunity cost of $220/mo payment and $320/mo fuel.

Ironically, as I've pointed out before, it wouldn't be cheaper to buy a $20K Jetta TDI and replicate the same scenario.

YMMV

Personally, any car not RWD should be off the list, and AWD cars just barely on the list. Sorry...every FWD car I've driven sucked. Even the vaunted GTI.

Lexus GS300/430. you can pick up an 06 or 07 for about 20K. Nice ride for sales. take the miles well.

Eric, yes the decision will ultimately come down to how much value I put on having a "nice" car.

Anyone actually own any of the cars mentioned with 100k+ miles that talk about first hand experience?

That's damn good advice.

Look at KBB.com, I think they've added some features about cost of ownership.

I looked at a Hyundai a few years ago (new) and what drove me away was the cost of collision insurance, it was so much more than a Toyota, like double.

I was in Vancouver, B.C. last week and drove a rental Ford Taurus SEL. It was a really nice looking car inside and out. The Microsoft Sync stuff and the pressure sensitive dash buttons were cool.

Quit kidding yourself, you want another BMW! Here's one locally but I'm sure a search in your area will produce the same:

Cars for Sale: 2007 BMW 335i w/ Premium Package in New Castle, PA 16101: Sedan Details - 321361092 - AutoTrader.com

I'm sure you could get it around 20k with some sweet talkin! The 335 is a great engine and very underated. A couple of mods with the turbo can produce more power then $1000's on a Porsche. If you buy anything else, you will one day realize its not a BMW and continue your search.:)