What I'm confused over is how people can go on for over a year until they come to the conclusion that the script just isn't working out for them.

It shouldn't take longer than two weeks to a month at the utmost to learn, experiment and conclude whether an application suite really works for your needs. And if you know what you're looking for, then it really shouldn't take longer than a couple days to evaluate if a CMS suite basically fits your needs.

In practice, if you're looking at developing see more anything you invest a bit into, I don't see how it's even practically possible to spend a year just in preparation of a website project — unless somehow you have unlimited funding and nothing else to do.