I probably tried when I was....well...in the single digits. It came off as being "not serious" to me then, because I just didn't catch the incisive parody happening because I'd not yet seen enough of the world. :P

I also picked the Watch books to try again, because it seemed like A) I'd like Vimes, B) it was a relatively self-contained intro, and C) folks with a-little-but-not-much power trying to help those with even less is one of my jams. :D

And I've heard good things about Going Postal! Thanks for the rec. I suspect that I will definitely be coming at the rest of Discworld from the "bureaucracy/infrastructure" angles, same as you.