The number one obstacle in automating anything is a naive attempt to mimic what hands do in the manual version. Which the machine really cannot do, since mechanical hands exist mostly as prosthetics and would require a human brain to make them really work their best anyway.
In the 1700s and before, clothing had to be hand-sewn by a tailor, and was super expensive. Most people owned at most two outfits. Or sometimes even just one. If it got damaged, they would hand-sew patches on to repair it, because they sure as hell couldn't afford another pair.
The tailors were all overworked, and sewing was a task outright itching for automation. And so starting in the 1600s, people attempted to create automated sewing machines, recognizing that such an invention would revolutionize the clothing industry. So they watched people hand sew, and tried to make a machine copy that movement. None of them worked. Always, something would jam, break down, or fail.
The real innovation didn't hit until 1846. The modern sewing machine uses both a needle and a bobbin to sew from both sides of the cloth at once in a way that would be quite impossible for a human to copy. And that is the lesson I would like to teach today: Mechanical movements are quite different from their human counterparts.
Or, let us take the vacuum cleaner. The human-wielded device is a cart, with a vertical attachment to a bag, and a handle for human direction. So to automate it, I suppose people first tried mechanical legs and arms, only to have the whole contraption repeatedly fall over. And then when automated vacuum cleaners were invented, they look nothing like the hand-pushed kind of yesteryear. They look more like a security droid from a sci-fi movie.
So when a task is automated, it often is accomplished in a way different way than it would be if a human was doing it. Imagine if there were no windshield wipers. If it rained, you'd regularly have to pull to the side of the road, get out of the car, and wipe the windows with a dry cloth. And you had better hope that you had a large supply of dry cloths. Imagine if then somebody tried to create a windshield wiper that moved a cloth and then wrung it out. Probably wouldn't work very well.
PS: The invention of the sewing machine has reduced a pair of the typical kind of shirt I wear to $7, and the cost of a pair of pants to $10. I own tens of each.