An example of this I've seen was the pay-TV service Tele1st. In 1984, this was billed as a way to rent first-run movies to consumers without having to go to the video store, by recording them onto tape overnight from an encrypted broadcast. Sounds simple, right? Only, the encryption was a PITA to set up: you needed to wire this big-ass box into your phone line and VCR, and prior to every broadcast of Tele1st, you would have to adjust a knob on the bottom of the unit so that the contrast matched a test pattern shown before the first movie. If you didn't do this, the encryption would fail. See for yourself: https://youtu.be/jR8YQu1HT8Y
Another example was the generous assumption that we would all be BASIC programmers. BASIC was pushed as the next essential household skill, like operating the TV or running the washer. V-tech toys came with reading, spelling, math, and BASIC. But in the end, all Grandma and Grandpa want is something that works when you press the button. They don't have the time or patience to figure out BASIC for a recipe keeper, that's what the modern-day App Store is for.
One of the strongest lessons Steve Jobs taught the tech world, is that the ease-of-use makes the difference between the IBM Simon and the culture-changing impact of the iPhone.