I used to love cruising around playing on the pins around my city. As soon as I got my own I realised how sub par those routed pins were and it makes it harder to enjoy them. But it also made me realise how much work it takes to get them playing perfectly.
In terms of pinball's success in arcades, kids do genuinely love to play pinball when they play on mine. They're besotted with it. But in the arcades their coins go straight to the shooting and driving games instead because they're not good enough at pinball to get their money's worth. Evidenced by a local arcade that has free play nights — kids love the pins on those nights because they're not afraid of wasting their money.
I think it's the high barrier to entry that explains why pinball machines can't attract new players. This combined with the fact that most people don't realise that there is far more to pinball than just keeping a ball bouncing around a playfield. The rules are impossible for newbies to understand and instruction cards only help players already well versed in pinball.
One of the things that video game designers have had to do to in recent years is invent ways to teach a player the game and ease them into it without needing to read a manual or work through tutorials. Pinball needs to solve the same problem in it's own way.