Once upon a time, if you wanted to go somewhere, you got there via muscle power: your own, someone else's, an animal's. Needless to say, getting anywhere was slow and, in a world in which everything is done with muscle power and food was not cheap, expensive. In that world, walking was expensive, which is why cities were so compact.
Then there was a world in which you could go somewhere on a train. Still pretty expensive, but much, much cheaper than any other option to date. So much cheaper, that it more or less wiped out all other long distance travel in a matter of a few decades. (You might be thinking, well, no one was walking across the country before that. And then you probably went, dur, never mind.)
The bicycle and, in short order, its evil spawn, the automobile, presented this country (since we had the most oil at the time) with a conundrum: continue to pay for each ride, which was basically pretty cheap, or spend a lot of money (possibly financed) to buy something that you could then travel around on or in for free, subject to fuel costs, maintenance costs, replacement costs, etc. While there have not necessarily been a lot of people spreadsheeting the costs as experienced at the time, the main perspective I've seen is a little odd. People from our car-world looking back at train fare try to figure out how ordinary, middling sorts of folk could afford to take vacations by train (which we know they did) -- the fare was an interesting chunk of money. But that's not really the right question. The question is why anyone would have financed a car, back in the day.
And I think all one really has to do is take a look at DVC to answer that question. Most people buying DVC don't really factor the ongoing dues into the cost calculation. Which is, in part, why there is a thriving resale market. But the draw, I think, then and now, is the Dream.