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Wow, your car history sounds a lot like mine (1974 Pontiac Grandville=>1995 Tercel=>1991 Toyota Hilux=>2002 Viper=>2005 Ram SRT-10=>2005 Honda Civic=>2013 Prius). Now, I look back at all the money I wasted on fuel (I drove the Viper cross-country multiple times) and laugh.
How much space do you need in the car? If I didn't regularly haul bikes to races and want something I can car camp in on long roadtrips, I probably would have gone with a 1st-gen Insight in retrospect. The Prius is a lot more flexible when it comes to hauling stuff, and the rate of battery failure is very low. If you don't mind having a funny-looking car, aeromodded Civics of pretty much any generation can return 50+mpg as well, depending on your driving.
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