I do think everyday behaviors have more single point of failures than they used to. The complexity has just gone up (with the example of needing to use the internet to get a parking spot) so almost by definition there are more ways it can go wrong.

That being said, I think you are just glorifying the past a bit. Watching on-demand television was impossible 15 years ago. People were still using tivo's you had to set ahead of time. I personally call my barber because its easier than the computer - and most places have both options.