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.
I really enjoyed Men at Arms and Jingo and Night Watch were also good. Basically I love the Watch subseries.
I mean, that’s like asking which child is your favourite (she says, having no children of her own). I honestly couldn’t pick a favourite - as others have said, the early ones aren’t great compared to the full body of work, but I love all of them.
Perhaps The Last Hero is my favourite owned book, if only because it’s a signed hardcover - I saw Terry speak in the early ‘00s, and had him sign it then.
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
Nightwatch and Going Postal. I'm also very fond of The Truth.
I love the whole discworld series. But if I had to pick a specific favourite I would pick Small Gods.
I have only read the first book so far but enjoyed it. I have a stack of books I want to get through and then I'll dive into more of the series. Any books I should be looking forward to, any I should skip?
The first couple are widely held to be the least good. I'd suggest jump into the Night Watch set (Guards Guards etc) or the Granny Weatherwax set (Wyrd Sisters etc) - they're widely held to be good starting points
(Edit: I appear to be fond of the phrase "widely held" today...)
Anything related to the fantasy genre