I think that what you need to look for when shopping for a Crossfire (or any used car) is a maintenance history. The Crossfire is really a quite reliable car, with typical Mercedes quality. There are a few common problems, but every one of them has been covered in great detail on this forum. If you buy a Crossfire and have an issue, you'll be able to come here for assistance in diagnosis, and usually will get detailed information on how to repair it. Most of the common problems can be fixed by a car enthusiast with average skills. If you can't do the job yourself, you'll be able to provide your mechanic with information that will make his job easier and will save you money.

You need to understand that your local Chrysler dealer probably is not the best place to take a Crossfire for repair. Many do not have Crossfire-certified technicians, and Chrysler dealers charge obscene prices for parts. You'll often buy the same parts for less at a Mercedes dealership, and independent mechanics who can work on a Mercedes SLK should be able to service your Crossfire.

The great thing about buying a 27,000 mile '05 roadster is that it has already taken a huge depreciation hit, and I think that prices are likely to stabilize and may even begin to rise in the future. I think that you will find maintenance costs to be quite reasonable, and you could probably put another 175,000 miles on that car with no serious issues.

Go for it.