29: 1953-1956 F-100
Released early in the pickup truck market, the second generation of the F-Series truck was a groundbreaking vehicle for Ford. The pickup truck was becoming more of a mainstream vehicle and Ford was beginning to sell them like hotcakes. The 1953-1956 F-100 had a lot of things that made it an interesting find. The cab had a new design on the interior that made the truck more comfortable to live with. Little features such as the truck bed made for a winning combination of functionality and cargo capacity. Reliability for an original version of this truck is iffy and can definitely take a lot of maintenance.
It is most common for these pickup trucks to have a modern engine swap, and if you can accomplish that, reliability is much improved. But if you’re going to for an original model, you can expect to pay a great deal of money to keep it on the road. The flathead V8 is an iconic powerplant and the styling is quintessential Ford, but this truck is quite the project to take on.