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 don't think you need a particular order.
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
I just started this series this year by picking up Going Postal, which I finished something like a month ago. I liked it a lot and as my "gateway drug" into the Discworld, I think I will always have good memories of it.
Nightwatch and Going Postal. I'm also very fond of The Truth.
Anything related to the fantasy genre