Oh I missed that! First build a bigger garage!

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2016 Corvette Stingray 2LT
1969 280SE
2023 Ram 1500
2007 Tiara 3200

Corvette.
In your price range you can have a wide range of model choices, from classic to fairly late model. They will be dependable, perform as well as all and better than most of the other choices, maintenance won't be a problem (Chebby dealers everywhere), fuel economy is decent and above all, there is a ready market for good, clean 'Vettes if and when you are ready to sell.
JMO of course.

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1983 M-B 240D-Gone too.
1976 M-B 300D-Departed.

"Good" is the worst enemy of "Great".

The Avanti II would be an interesting choice, particularly those from the mid '70's on up which were powered by a small block Chevy.

For $25k you could get something like this:




Or one of these for much less, and you get the V12.

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2016 Corvette Stingray 2LT
1969 280SE
2023 Ram 1500
2007 Tiara 3200

Too long, aren't they?

The Mercedes? The CL's are based on the S class, so they are big cars.

But if you want a good GT car which it sounds like he does, IMHO they are the best. Unless you want to poney up for something from Italy. Like a Ferrari 456.

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2016 Corvette Stingray 2LT
1969 280SE
2023 Ram 1500
2007 Tiara 3200

The maximum length limit is a real killer. For domestic vehicles, you're limited to a pony car, which can be a fun, but not necessarily refined, ride. Perhaps a '67-'73 Mercury Cougar, which can be a bit heavier and softer riding than a comparably aged Mustang. I still like the Avanti II, as it was a handbuilt vehicle using humble drivetrain components. A fiberglass body, so rust is not a consideration in that respect, but steel sections under the passenger comparment, known as "hog troughs" to Avanti buffs for their unusual shape, can rot out, but replacement panels are available. I'm 6'2" and was comfortable behind the wheel (the example I was in did not have a sunroof, which helped). If you can fit behind the wheel of a '71 - '81 Camaro, you should be able to fit in this car.

How about a last-gen Saab 9-3 Viggen?

Ok, I've found your car: http://www.youtube.com/watch?v=Pe2tC_s-eZM

(?!!?)

Some people have too much time on their hands. That business of going down the road half sideways with both sets of wheels turned parallel was a trip. Seems like they need two drivers.

One thing they didn't show was the cops stopping them.

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Te futueo et caballum tuum

1986 300SDL, 362K
1984 300D, 138K

A second-gen Corvair IS an interesting choice, much better than the first-gen Corvairs, which exhibited some interesting rear-wheel camber changes during spirited driving.

I was a Corvair fan. Mind you the zenith of Corvair-dom happened in 1966, making the best examples over 40 years old. Also wifey would have to be OK with no A/C, and seats that are as flat as Kansas. Oh, and power nothing.

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1985 380SE Blue/Blue - 230,000 miles
2012 Subaru Forester 5-speed
2005 Toyota Sienna
2004 Chrysler Sebring convertible
1999 Toyota Tacoma

I drove my first car at the age of seven, a 1962 Corvair 600 2-door.

Was that experience the absolute nadir of your childhood?

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LOL! Well, it was actually quite enjoyable. Despite the lack of any power assists, I found it to be an extremely easy car to drive. Much less intimidating than my father's black 1964 Chrysler Imperial Crown Coupe.