In Will's Boy, Wright Morris gives some pages to a trip from Chicago to California in 1927. He and his father began with an Essex, purchased used for $125. This lasted them to Springfield, Illinois, where the knock of a bad bearing could no longer be ignored. They sold the car for $60, and took buses to Kansas City, Missouri. There they purchased a 1921 Studebaker for $165, recruited some paying passengers, and set out. On the grade down to the Missouri River, the gearbox fell off. The Morrises immediately swapped this, as is, for a 1919 Buick. The Buick, though not the passengers, lasted until a missed curve in the California desert, where it stuck in the soft sand.
The car purchased for the return trip, a Marmon, took them to Lake Village, Arkansas, where it dropped its transmission. There was no time to consider repairs or a trade in, for it was almost at once swept away in the great Mississippi flood of 1928, when the levee broke upstream. Along the way it required a great deal of improvised tire repair--fitting an old tire, its bead removed, over a flat one--and it cast its right front wheel near Deming, New Mexico. To be sure, they had done a good deal of driving over mule tracks early on the trip.
The cars made since about 1980 tend to be hard to break. Before that, it helped to know a lot about cars, or to know a good mechanic. A friend of my father's chipped in with some friends to buy a used car for the trip back east from a field camp about 1950; they traveled with spare parts, and when a piston shot out through the hood they were ready to replace it. The late 1940s or early 1950s may have been the nadir of auto quality, for civilian production had been suspended for WW II, and only so many American could afford new cars.
Tires have improved a great deal in my memory. Beginning the January after I got my driver's license, I averaged a flat tire a month through August. I was the better prepared, then, when on a summer job I changed a flat tire on a company car, let down the jack, and saw the spare go flat. In the last twenty-five year I recall changing two flats our cars, one holed by a screw from the Metro construction on Georgia Avenue, one cut by a granite curb at Connecticut and California.