I've never bought new. My dad did several times (first in 1953 with an MGTF-cool car), but not since 1971 (Ford Maverick Grabber 302-also a cool car-Dad used to have some taste before he started buying Cadillacs). The closest I've had to "new" were a 2006 Kawasaki in near perfect condition that I bought for $2600 in 2011, and my '83 300D that I had major body and paint work done on this year. The '06 was run over by a truck while it was parked five months after I bought it, and the insurance settlement worked out well for me. The '83 got its first new door ding within two weeks of the repaint. Careless bastids! It still looks a lot better than it did before, but the rear suspension is asking for new bushings all around, and the steering box has a huge dead spot on center. Sometimes I want to give up and buy new/newish, but a quick check on the cost of fixing mine vs the cost of a newer vehicle tells me I'll be driving the W123 for a long time yet.

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Whoever said there's nothing more expensive than a cheap Mercedes never had a cheap Jaguar.

83 300D Turbo with manual conversion, early W126 vented front rotors and H4 headlights 401,xxx miles
08 Suzuki GSX-R600 M4 Slip-on 26,xxx miles
88 Jaguar XJS V12 94,xxx miles. Work in progress.
99 Mazda Miata 183,xxx miles.