When I was test driving my '67 Mustang before I bought it, the first thing that happened after I started it was the driver's side visor flopping down. I said "Charming!". The radio didn't work. The convertible top liner was tattered as hell. After the test drive, I told the salesman (the car was at a dealership, oddly) "This car is a piece of shit. I'll take it".
I like giving my passengers tours of all the things in my car that don't work, like the heater, radio, temp gauge, voltage meter, parking brake light, etc. The slightly sagging passenger window. The tick of a small exhaust leak. I don't mind this stuff; it's an old car, I like the little quirks (although I need that leak and temp gauge fixed). What I DON'T like, are the rattles and squeaks coming from my door panels. Holy shit it's annoying.
So that made me wonder...where do you draw the line between endearing and annoying when it comes to a beat up car? Some people would find my car's little quirks annoying as hell. I like them, and when I eventually fix them I know I'm going to miss them in a strange way. What about you?