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I'll preface this with the statement that all my vehicles have been acquired used. I'm only going to rate the daily drivers (the 911 doesn't count).
WORST: '87 Subaru GL Wagon 4WD -Gutless, carb kept failing, transmission shifted funny, didn't handle well, parts were expensive and hard to find (and I owned this in the nineties), interior fit/finish sub-par, limited traction in the snow even when the 4WD was turned on. Goofy ergonomics - everything seemed to operated backward from what I expected. That car and I didn't get along.
BEST: '92 Audi 100 - Plenty of power, would cruise effortlessly all day at 75-80mph and get 30mpg (in the days before ethanol gas), comfortable, solid, handled very well and great traction in inclement weather (and snow) although it was only FWD. Repairs were few and far between. This car was easy to maintain and almost always a joy to drive. I kept this one almost 20 years.
Somewhere in-between (in order from bad to good):
'99 Audi A6 Avant
'66 Dodge pickup
'76 Audi Fox (kept this one 20+ years - got into a lot of trouble/fun with this little car...)
'07 Dodge 1500 pickup
'01 Audi A6 Avant
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