When things are too easy, they lose meaning. I think this is probably a sensory matter, and I think it's correlated with satisfaction. The better you can sense an interaction, the more satisfaction you get from the interaction.
Examples:
- Looking at the Mona Lisa is more satisfying than looking at a blank canvas.
- Watching a celluoid movie is more satisfying than watching a digital movie. (Most people aren't attuned to the difference, and sometimes I can't even tell, so it's hard to distinguish this from a preference.)
- Driving stick is more satsifying than driving an automatic. It's even reflected in language. What's more fun to say? Push it in park or jam 'er down in gear?
When you can't sense an activity, you lose your sense of particpation in the activity. When you lose your sense of particiatpion, you feel less like the driver and more and more like a passenger. The driver is someone important. A passenger could be anybody.
There's something missing from a frictionless life. Maybe this is why some people prefer a fraught relationship to no relationship at all.
That said, people obviously prefer automatics to stickshifts. But I think that's because most people consider driving a necessary evil, and the people who lament the demise of the stickshift are predisposed to find driving fun.
So making things easier is good when it eliminates a necessary evil, but people disagree on what constitutes a necessary evil.