This may be a dumb question, but if I want to try to dip my feet in to the series, is it best to read in chronological order or some other order? I haven't started yet, but it's on my list.
I just borrowed books at random from the library as they became available, so the order won't really affect your enjoyment imho. Pratchett does a good job of quickly reintroducing concepts and characters even in later books, so you're never ever missing actual critical information