My first car the 1960 Simca Aronde with the Flash engine has to rank up there. Short lived engine and fragile transmission had me changing the engine three times and replacing first gear in the tranny only to have it broken almost immediately then driving it three or four more years through college with a chipped first gear. Great ride and handling but mechanically rubbish.

My second car was a 61 Bugeye sprite. It was close to tied with the Simca for worst ever but that perhaps was mainly because it was so comprehensively worn out when I got it....but it was very very fun to drive if you could keep oil in it.

The 66 Corvair with the 110 motor I had later was a lot better car mechanically but the heater was rubbish on it.

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[SIGPIC] Diesel loving autocrossing grandpa Architect. 08 Dodge 3/4 ton with Cummins & six speed; I have had about 35 benzes. I have a 39 Studebaker Coupe Express pickup in which I have had installed a 617 turbo and a five speed manual.[SIGPIC]

..I also have a 427 Cobra replica with an aluminum chassis.