There is something timeless and endearing about a classic American pickup. The owners/drivers don't speed like a black Audi or cut you off accidentally like a Prius -- and the simple sight of these always puts a smile on my face. I don't have an old round fender pickup in my garage, but if I did, it'd look like this 1953 Ford F-250 Pickup offered for $7,500 in Naples, FL via craigslist. Tip from Dascpcu.
The second generation F-Series was released for the 1953 model year with a package that was larger, faster, and generally mo' better. This '53 F-250 is the last year for the flathead V8 power, which I think is a plus for long term collectability. The Y-block V8 might be a better engine for everyday use, but it just doesn't have the cachet of Ford's flatty that was introduced as the worlds first mass produced V8 in 1932 -- and this was the least year you could get one in a domestic Ford.
See a better car for towing a Chevy? firstname.lastname@example.org