mason i see what you are saying here, but the idea behind getting something that is cheap, reliable, and safe is to provide the driving experience without worrying about whether of not yu put that big dent in the trunk/hatch or busted out the grill.
I also suggest the samething to anyone looking for their first car. Mine was a 1971 Ford F100 pickup (wish I still had it now) which I paid for with a paper route and did a little work to get it on the road. I wrecked several cars, unfortunately the one that I totalled was a nice car in nearly mint condition. I still wish I had waited a little longer to get a "nice" car and acquired the driving experience first.
see..the thing with pickups is that they handle like poop in any bad weather. 25 years ago, i had my first pickup...a 69 chevy c-10. mannnn was that thing fun in the snow...350 2wd, 3 speed on the floor. i used to go into empty parking lots, back roads with nothign parked along the sides, and just throw that old POS around.
you kind of can't get away with that these days though.
i still think for everything he's wanting, a honda civic, or a toyota camry will fit the bill very nicely.
i had a customer..had 3 camrys in the family. the lowest mileage one was just over 300k. the highest one was about 370k or so. there's a guy that comes in to get gas, has 375 on his 2000 camry.