I have 1998 car, it's commuter which I still enjoy driving. I bought it 5 years ago for $2600 with 85000 miles on it. Currently it has 172000 miles. I drive to work 25 miles each way (no, I can't move to Palo Alto where I work), do weekend grocery trips for/with my grandma, and once or twice a year my girlfriend and I go on road trips.
The main problem with it - oil leaks quite badly from the engine, so have to add a quart of oil every couple weeks. Other than this it's in tip-top mechanical condition. Next maintenance will be due on 200000 miles (timing belt and maybe clutch). I asked mechanic where does it leak from, he grinned and said "everywhere". It's not a big deal for me since I routinely check all fluids every weekend. But here comes social aspect - it leaves oil on my company's parking lot. Which causes minor discomfort about polluting environment. However, I'm afraid sooner or later they will figure me out, and it will be quite embarrassing moment :)
I can afford any new car, yet realize how stupid it will be financial wise. It costs me 16 cents per mile to run - including fuel, service, insurance and depreciation. From time to time I run numbers on alternatives - nothing can beat it. However, sometimes I feel like I'm crossing a border line between frugal and cheap. Comrades, please advise.