I bought my 2000 300M brand new (ordered from the factory) and have had nothing but a great experience with it. The car was not as fast as my twin-turbo Stealth but very few cars could match that performance. But it has room. I am tall and even with the driver's seat in my driving position, I can sit comfortably in the back seat without my legs touching the driver's seat. The ride is very comfortable without being out-of-touch. The reliability has been nothing short of amazing. Other than normal wear parts (tires, break pads, bushings, wiper blades, air filters, etc) the car has not needed any significant work. Nearly 200,000 miles!
After 10 years of loving attention, my '2000 M still turns heads. With factory chrome wheels and slightly fatter tires on the 17" wheels, it looks very contemporary. Most newer cars still retain the look the 330M pioneered in 1999. No significant problems - Except for tires, all original equipment. (Almost all highway driving). I'd buy it again.
I have put 248,849 miles on my 300M, still has the original engine and transmission. I have to say I did keep up with the oil changes, most of my driving was highway driving for about 100 per day. The 300M has served me well. The problems I have had with the car was that all 4 of the automatic door locks needed to be replaced, warranty handled the cost of 2 and I footed the cost for the other 2. I even tried to get them to replace the last 2 before the door locks failed and the warranty ran out but no luck. Also the air-conditioner required about 1,000 dollars of work to get fix after 7 years. If those items didn't go wrong I may have gotten another. Surprise, but I'm driving a Prius now.
I was stupid enough to go from owning a reliable, quality built Honda Accord to purchasing a Chrysler 300M in late 1999. Big mistake. I was suckered into believing in American made and falling for the cool exterior design...what was underneath was pure junk. I can't tell you the amount of money, worry, disappointment, and absolute frustration this vehicle has brought me. I remember bringing it home thinking I would baby it and have it for years...imagining it could be considered a classic some day...what a naive notion that was. It's a Chrysler stupid!!!! USA Auto Execs dismissed Dr. Deming who wanted to teach them about Total Quality Systems. So he went to Japan where they listened.
I have had the car for 4 years so far. Bought it in 2008 with 77K miles on it. Since then I've had to replace the power door lock on the driver's side, the front suspension control arms, turn signal flasher and the oil pressure switch. The a/c also doesn't blow cold because there's a leak in the a/c system (the condenser, compressor, or evaporator). Not sure if I want to spend the money to fix the a/c. Also the interior instrument panel lights were flashing, so I replaced the headlight/dimmer switch assembly with a used on purchased from eBay (that fixed the problem). However the car has strong acceleration and smooth engine performance, but Chrysler needs to focus on reliability.