That's a rose-tinted view of things. There's plenty of dirt-cheap land just outside all but the biggest American towns, but no drive-ins on them. Seriously, without knowing you, chances are you and a couple of friends could pool your savings and buy a plot and setup a drive-in theatre. But chances are you'd fail. Land increasing in value is far from the only thing that changed that affected drive-ins. A car (and especially the sound options in one) is far from an ideal place to enjoy a movie from, streaming (or before that, renting a video or just watching on broadcast TV) on a large colour TV is much, much better. Modern, multiplex theatres provide a technically far, far superior experience to either. Attitudes to pre-marital sex have decreased the value of having somewhere to legitimately park in the dark for an extended period.

Many analogous things are true for toy stores and hardware stores etc. And people are banding together to support things that aren't commercially viable, the closest thing to hardware stores in this regard is probably hacker spaces.

And to answer your question directly, yes, I strongly prefer to live in a society where businesses are allowed to fail when they've run their course rather than being kept on life-support for vague past-romantic reasons.